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

HRID 337019

反応式

HRID 337019 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d4188331ee3846b4b114635ecbbc573a
出典データセット
uspto-grants-2014_11
特許番号
US08889692B2

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