Ammonium Hydroxide → 2-Amino-5-methoxybenzamide

HRID 1014164노트

반응식

HRID 1014164 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:11]C(=O)[O:9][C:8](=O)[C:7]=2[CH:14]=1.[OH-].[NH4+:16]>C(OCC)(=O)C>[NH2:11][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:7]=1[C:8]([NH2:16])=[O:9]

참가 물질

4

반응물 2

HCID 14923Ammonium HydroxideHCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

생성물 1

HCID 203382172-Amino-5-methoxybenzamide수율 53%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

6-methoxy-2H-3,1-benzoxazine-2,4(1H)-dione (3.0 g, 16 mmol, Trans World Chemicals) was treated directly with 27% aqueous ammonium hydroxide. After one hour the organic phase was diluted with ethyl acetate, washed twice with aqueous sodium bicarbonate and saturated aqueous sodium chloride, and dried over sodium sulfate. Filtration and removal of the residual solvent gave 2-amino-5-(methyloxy)benzamide as a white solid (1.42 g, 53% Yield);. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.63 (s, 3 H), 6.07 (s, 2 H), 6.60 (d, J=8.97 Hz, 1 H), 6.79 (dd, J=8.79, 2.93 Hz, 1 H), 7.03 (s, 1 H), 7.06 (d, J=2.93 Hz, 1 H), 7.71 (s, 1 H).

후처리

  1. washwashed twice with aqueous sodium bicarbonate and saturated aqueous sodium chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltration and removal of the residual solvent

출처 및 근거

ORD 기록
ord-c1e55b81dead4a81bbf7f7967a06e27a
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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