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

HRID 337019

Reaction equation

HRID 337019 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d4188331ee3846b4b114635ecbbc573a
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Linked notes

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