Water → 5-(Benzyloxy)-4-methoxy-2-nitrobenzamide

HRID 1406992ノート

反応式

HRID 1406992 の反応式
[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1.C(Cl)(=O)C(Cl)=O.O.[OH-].[NH4+:31]>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7]([NH2:31])=[O:8])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1

参加物

7

反応物 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 8212205-(Benzyloxy)-4-methoxy-2-nitrobenzoic acid

生成物 1

HCID 593618645-(Benzyloxy)-4-methoxy-2-nitrobenzamide収率 65%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 4-methoxy-5-benzyloxy-2-nitrobenzoic acid (10.0 g, 33.3 mmol) in anhydrous THF (100 mL) was added oxalyl chloride (4.90 mL, 56.2 mmol) followed by one drop of anhydrous DMF. The mixture was stirred at RT for 16 h, upon which the mixture was poured into water (300 mL) and ammonium hydroxide (50 mL). A solid was separated out, which was collected by filtration and dried under vacuo. The solid was taken up in refluxing methanol (500 mL) and the insoluble solid was collected via filtration and dried under vacuum to give 4-methoxy-5-benzyloxy-2-nitrobenzamide (6.50 g, 21.5 mmol, 65%). HPLC retention time 6.154 min.

後処理

  1. customA solid was separated out
  2. filtrationwhich was collected by filtration
  3. customdried under vacuo
  4. temperaturein refluxing methanol (500 mL)
  5. filtrationthe insoluble solid was collected via filtration
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-7f9d7423485c40f0b7d001172005e013
出典データセット
uspto-grants-2014_12
特許番号
US08916576B2

反応ノート

読み込み中…