Hydrochloric Acid → 2-Amino-3-(benzyloxy)-6-methoxybenzamide

HRID 922402노트

반응식

HRID 922402 반응식
[CH2:1]([O:8][C:9]1[C:10]([N+:20]([O-])=O)=[C:11]([C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:12]([NH2:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>CCO.[Fe]>[NH2:20][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=[C:15]([O:18][CH3:19])[C:11]=1[C:12]([NH2:14])=[O:13]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 867193593-(Benzyloxy)-6-methoxy-2-nitrobenzamide

생성물 1

HCID 867193602-Amino-3-(benzyloxy)-6-methoxybenzamide

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3-(benzyloxy)-6-methoxy-2-nitrobenzamide (10, 0.34 g. 1.1 mmol), iron powder (0.44 g, 7.7 mmol) and concentrated hydrochloric acid (80 mL) in EtOH (4 mL)/water (0.4 mL) was heated at 90° C. for 75 min. The reaction mixture was cooled to room temperature, filtered through Celite and concentrated. The residue was dissolved in EtOAc washed with saturated NaHCO3 solution, dried over Na2SO4, filtered, and concentrated. Purification by silica gel chromatography eluting with 0-10% MeOH in CH2Cl2 afforded the title compound along with its regioisomer (0.267 g, 87%) as a tan solid: 1H NMR (500 MHz, CDCl3) δ 7.83 (br s, 1H), 7.47-7.32 (m, 5H), 6.77 (d, J=8.8 Hz, 1H), 6.60 (br s, 2H), 6.06 (d, J=8.8 Hz, 1H), 5.51 (br s, 1H), 5.04 (s, 2H), 3.85 (s, 3H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography
  10. washeluting with 0-10% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-57c23484125c4aeb8525e7e9b8c4fbd6
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278940B2

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