5-(Benzyloxy)-4-methoxy-2-nitrobenzamide → 2-Amino-5-(benzyloxy)-4-methoxybenzamide

HRID 1406993노트

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HRID 1406993 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]([NH2:9])=[O:8])=[C:5]([N+:20]([O-])=O)[CH:4]=1>C(O)(=O)C.CO.[Fe]>[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]([NH2:9])=[O:8])=[C:5]([NH2:20])[CH:4]=1

참가 물질

4

반응물 1

HCID 593618645-(Benzyloxy)-4-methoxy-2-nitrobenzamide

생성물 1

HCID 593619042-Amino-5-(benzyloxy)-4-methoxybenzamide수율 87.2%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 10129899Acetic acid methanol용매

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온도
85 °C

실험 절차

A mixture of 4-methoxy-5-benzyloxy-2-nitrobenzamide (6.60 g, 21.9 mmol) and iron powder (8.14 g, 0.146 mol) in acetic acid/methanol (80 mL/80 mL) was heated at 85±5° C. for 1.5 h. The reaction mixture was allowed to cool to RT and the iron was removed by filtration, and volatiles were removed in vacuo. The residue was taken up in sat. sodium bicarbonate and the mixture was extracted with ethyl acetate (600 mL×3). The combined organic layers were washed with water (1×150 mL), brine (1×150 mL), dried (Na2SO4), filtered and concentrated in vacuo to give 4-methoxy-5-benzyloxy-2-aminobenzamide (5.2 g, 19.1 mmol, 87%). MS 273.2. (M+). HPLC retention time 4.585 min.

후처리

  1. temperatureto cool to RT
  2. customthe iron was removed by filtration, and volatiles
  3. customwere removed in vacuo
  4. extractionthe mixture was extracted with ethyl acetate (600 mL×3)
  5. washThe combined organic layers were washed with water (1×150 mL), brine (1×150 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-86763c89e7804adea2ae1adc3878146c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916576B2

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