Preparing crystalline form-III of benzenediol for treating psoriasis involves reacting dihydroxybenzoic acid with dimethyl sulfate, in potassium carbonate, reacting dimethoxy benzoate with isopropyl bromide, reducing dimethoxy benzoate with vitride in toluene, oxidizing dimethoxyphenyl methanol
	BOTIKA S P; PRADEEP R; RAMPRASAD A K; NAGARAJU C
	2023-08-30
专利权人	MAITHRI DRUGS PRIVATE LTD (MAIT-Non-standard)
申请日期	2023-08-30
专利号	IN202341058037-A
成果简介	NOVELTY - Preparing crystalline form-III of phenyl ethenyl-1,3-benzenediol (I) involves (a) reacting dihydroxybenzoic acid (II) with dimethyl sulfate, in potassium carbonate, acetone to provide dimethoxy benzoate (III); (b) reacting the dimethoxy benzoate (III) with isopropyl bromide, aluminum chloride in dichloromethane to provide [Methyl-4-isopropyl-3,5- dimethoxy benzoate] (IV), (c) reducing the [Methyl-4-isopropyl-3,5- dimethoxy benzoate] (IV) obtained with vitride in toluene to provide ((4-isopropyl-3,5-dimethoxyphenyl)methanol) (V), (d) oxidizing the ((4-isopropyl-3,5-dimethoxyphenyl)methanol) (V) using manganese dioxide in dichloromethane, solvent to provide dimethoxy benzaldehyde (VI), (e) reacting the dimethoxy benzaldehyde (VI) with diethyl phenylphosphonate (VII) using potassium hydroxide base in dimethyl formamide solvent to provide dimethoxy-5- styrylbenzene (VIII), (f) deprotecting dimethoxy-5- styrylbenzene (VIII) with aluminum chloride, triethyl amine in toluene to provide (I). USE - Process for preparing crystalline form-III of 2-(1-Methylethyl)-5-[(1E)-2- phenyl ethenyl]-1,3-benzenediol (I), for treating psoriasis and atopic dermatitis. No biological data given. ADVANTAGE - The (I) has high purity of 99%. DETAILED DESCRIPTION - Preparing crystalline form-III of 2-(1-Methylethyl)-5-[(1E)-2- phenyl ethenyl]-1,3-benzenediol (I) involves (a) reacting the 3,5-dihydroxybenzoic acid (II) with dimethyl sulfate, in presence of potassium carbonate in acetone to provide the [methyl-3,5-dimethoxy benzoate] of formula (III), (b) reacting the [methyl-3,5-dimethoxy benzoate] (III) with isopropyl bromide, aluminum chloride in dichloromethane to provide the [Methyl-4-isopropyl-3,5- dimethoxy benzoate] of formula (IV), (c) reducing the [Methyl-4-isopropyl-3,5- dimethoxy benzoate] -3a obtained with vitride in toluene to provide the ((4-isopropyl-3,5-dimethoxyphenyl)methanol) of formula (V), (d) oxidizing the ((4-isopropyl-3,5-dimethoxyphenyl)methanol) (V) using manganese dioxide in dichloromethane, solvent to provide 4-isopropyl-3,5-dimethoxy benzaldehyde of formula (VI), (e) reacting the 4-isopropyl-3,5-dimethoxy benzaldehyde (VI) with Diethyl phenylphosphonate of formula (VII) using potassium hydroxide (KOH) base in dimethyl formamide solvent to provide (E)-2-isopropyl-1,3-dimethoxy-5- styrylbenzene of formula (VIII), (f) deprotecting the (E)-2-isopropyl-1,3-dimethoxy-5- styrylbenzene (VIII) with aluminum chloride, triethyl amine in toluene to provide (I), (g) purifying the (I) in methyl tert butyl ether and n-heptane to provide pure crystalline form III of (I). An INDEPENDENT CLAIM is included for a process for preparation of crystalline form 1 of (I) which involves (a) reacting the 3,5-dihydroxybenzoic acid (II) with dimethyl sulfate, in presence of potassium carbonate in acetone to provide the [methyl-3,5-dimethoxy benzoate] of formula (III), (b) reacting the [methyl-3,5-dimethoxy benzoate] (III) with isopropyl bromide, aluminum chloride in dichloromethane to provide the [Methyl-4-isopropyl-3,5- dimethoxy benzoate] of formula (IV), (c) reducing the [Methyl-4-isopropyl-3,5- dimethoxy benzoate] -3a obtained with vitride in toluene to provide the ((4-isopropyl-3,5-dimethoxyphenyl)methanol) of formula (V), (d) oxidizing the ((4-isopropyl-3,5-dimethoxyphenyl)methanol) (V) using manganese dioxide in dichloromethane, solvent to provide 4-isopropyl-3,5-dimethoxy benzaldehyde of formula (VI), (e) reacting the 4-isopropyl-3,5-dimethoxy benzaldehyde (VI) with Diethyl phenylphosphonate of formula (VII) using potassium hydroxide (KOH) base in dimethyl formamide solvent to provide (E)-2-isopropyl-1,3-dimethoxy-5- styrylbenzene of formula (VIII), (f) deprotecting the (E)-2-isopropyl-1,3-dimethoxy-5- styrylbenzene (VIII) with aluminum chloride, triethyl amine in toluene to provide (I); (g) stirring the (VIII) obtained in isopropanol, (h) adding the solution obtained to water, (i) isolating the pure crystalline form 1 of (i).
IPC 分类号	A61K-031/05 ; A61K-047/06 ; A61K-047/10 ; A61K-009/06 ; A61K-009/10 ; A61K-009/107 ; A61K-009/113 ; C07D-405/04
国家	印度
专业领域	医药卫生
语种	英语
成果类型	专利
文献类型	科技成果
条目标识符	http://119.78.100.226:8889/handle/3KE4DYBR/20617
专题	中国科学院新疆生态与地理研究所
作者单位	MAITHRI DRUGS PRIVATE LTD (MAIT-Non-standard)
推荐引用方式 GB/T 7714	BOTIKA S P,PRADEEP R,RAMPRASAD A K,et al. Preparing crystalline form-III of benzenediol for treating psoriasis involves reacting dihydroxybenzoic acid with dimethyl sulfate, in potassium carbonate, reacting dimethoxy benzoate with isopropyl bromide, reducing dimethoxy benzoate with vitride in toluene, oxidizing dimethoxyphenyl methanol. IN202341058037-A[P]. 2023.

条目包含的文件
条目无相关文件。

除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。