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

HRID 1406992노트

반응식

HRID 1406992 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 593618645-(Benzyloxy)-4-methoxy-2-nitrobenzamide수율 65%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7f9d7423485c40f0b7d001172005e013
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916576B2

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