Methanamine, N-methoxy-, hydrochloride (1:1) → 4-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide

HRID 238874

反応式

HRID 238874 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[OH:11].Cl.[CH3:13][NH:14][O:15][CH3:16]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([O:15][CH3:16])[CH3:13])=[O:8])=[CH:4][C:3]=1[OH:11]

参加物

4

反応物 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5936354-Fluoro-3-hydroxybenzoic acid

生成物 1

HCID 594590524-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 4-fluoro-3-hydroxybenzoic acid (1.49 g, 9.55 mmol) in DCM (40 mL) was added TEA (1.2 mL, 8.61 mmol) followed by N,O-dimethylhydroxylamine hydrochloride (1.12 g, 11.5 mmol). The reaction mixture was stirred at room temperature for 3 h, then diluted with DCM, washed with water twice, dried over Na2SO4, filtered and concentrated to yield 4-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide as a colorless oil (1.90 g, 100% yield). LCMS: RT=0.89 min [M+H] 200.10 (Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm).

後処理

  1. washwashed with water twice
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-a63353c108514aaa90368f012e009f9a
出典データセット
uspto-grants-2014_02
特許番号
US08642576B2

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