Water → Methyl 3-[(cyanomethyl)amino]-4-methylbenzoate

HRID 1697279

반응식

HRID 1697279 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[CH:13]([N:16](CC)C(C)C)(C)[CH3:14].BrCC#N.O>O1CCCC1>[C:13]([CH2:14][NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6])#[N:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 337778Methyl 3-amino-4-methylbenzoate

생성물 1

HCID 86663236Methyl 3-[(cyanomethyl)amino]-4-methylbenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 3-amino-4-methyl-benzoic acid, methyl ester (10.0 g) in dry tetrahydrofuran was added N,N-diisopropylethylamine (12.6 mL) followed by the addition of bromoacetonitrile (5.1 mL). The reaction was heated at reflux under an atmosphere of nitrogen with stirring for 12 h. Water was added and the mixture extracted with ethyl acetate. The pooled organics were washed with brine, dried (MgSO4), filtered and the solvent removed under reduced pressure to afford the subtitle compound as a solid (12.4 g).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux under an atmosphere of nitrogen
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe pooled organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-1ef404d82bf24ea5b4a2e4db7165d62b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163905B2

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