Ammonium Hydroxide → 2-Amino-5-methoxybenzamide

HRID 1014164ノート

反応式

HRID 1014164 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 203382172-Amino-5-methoxybenzamide収率 53%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c1e55b81dead4a81bbf7f7967a06e27a
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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