4-Hydroxy-3-nitrobenzaldehyde → [5-(1H-Indol-2-yl)-2-methoxy-phenyl]-(4-hydroxy-3-nitro-benzyl)-amine

HRID 25526

反応式

HRID 25526 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH2:28])[CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH:28][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=2)[CH:27]=1

参加物

7

反応物 4

HCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99002045-(1H-indol-2-yl)-2-methoxy-phenylamine

生成物 1

HCID 10293687[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-(4-hydroxy-3-nitro-benzyl)-amine収率 39.4%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Hydroxy-3-nitrobenzaldehyde (0.334 g, 2.0 mmol) was added to a stirred mixture of 5-(1H-indol-2-yl)-2-methoxy-phenylamine (0.476 g, 2.0 mmol) in methylene chloride (125 mL), followed by acetic acid (0.2 g). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.46 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution was stirred at room temperature for 3 days. Saturoted aqueous sodium bicarbonate solution (100 mL) was added and the mixture was stirred for 2 hours. The mixture was shaken, the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give a brown gum. Recrystallization from methanol gave the product (307 mg), mp 165-166° C.

後処理

  1. stirringthe resulting homogeneous solution was stirred at room temperature for 3 days
  2. stirringthe mixture was stirred for 2 hours
  3. stirringThe mixture was shaken
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customto give a brown gum
  8. customRecrystallization from methanol

出典と根拠

ORDレコード
ord-4a09980cb5f343ce9598f05e969b4d52
出典データセット
uspto-grants-2005_02
特許番号
US06858739B2

関連ノート

読み込み中…