Ethanol → 4-(2-amino-4,5-dimethoxybenzoyl)-1-(4-methoxybenzyl)-1H-1,2,3-triazole-5-carboxylic acid

HRID 841956ノート

反応式

HRID 841956 の反応式
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[C:12]([C:13]([OH:15])=[O:14])=[C:11]([C:16](=[O:30])[C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[CH:19][C:18]=3[N+:27]([O-])=O)[N:10]=[N:9]2)=[CH:5][CH:4]=1.C(O)C.C(OCC)(=O)C.[H][H]>[C].[Pd].C(Cl)Cl>[NH2:27][C:18]1[CH:19]=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:17]=1[C:16]([C:11]1[N:10]=[N:9][N:8]([CH2:7][C:6]2[CH:31]=[CH:32][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:12]=1[C:13]([OH:15])=[O:14])=[O:30]

参加物

7

反応物 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 222225801-(4-methoxybenzyl)-4-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-5-carboxylic acidHCID 178418361HCID 178418361、化合物

生成物 1

HCID 222226424-(2-amino-4,5-dimethoxybenzoyl)-1-(4-methoxybenzyl)-1H-1,2,3-triazole-5-carboxylic acid収率 100%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

A 1 N aqueous sodium hydroxide solution (13 ml) was added to a solution of ethyl 1-(4-methoxybenzyl)-4-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-5-carboxylate (b-1) (3.04 g, 6.46 mmol), prepared in step (b), in tetrahydrofuran (40 ml). The mixture was stirred at room temperature for 3.5 hr. The reaction solution was diluted with ether, and water was added thereto. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate, followed by washing with water and saturated brine solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 1-(4-methoxybenzyl)-4-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-5-carboxyic acid as light yellow oil (c-1′:LP) (2.55 g, 89%). The resultant 1-(4-methoxybenzyl)-4-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-5-carboxylic acid (c-1′:LP) (1.07 g, 2.42 mmol) was dissolved in a mixed solvent composed of ethanol (50 ml) and ethyl acetate (50 ml). 10% palladium-carbon (129 mg) was added thereto. The mixture was stirred in a hydrogen atmosphere at room temperature for 4 hr. Methylene chloride was added to the reaction solution to dissolve the precipitated crystal, followed by filtration through Celite. The filtrate was concentrated under reduced pressure to give 4-(2-amino-4,5-dimethoxybenzoyl)-1-(4-methoxybenzyl)-1H-1,2,3-triazole-5-carboxylic acid (c-1: LP) (1.06 g, 100%).

後処理

  1. dissolutionto dissolve the precipitated crystal
  2. filtrationfollowed by filtration through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-3ace6e80337743c4b4daa0b7c2194983
出典データセット
uspto-grants-2002_04
特許番号
US06372735B1

反応ノート

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