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

HRID 2070698Notes

Reaction equation

HRID 2070698 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-1fde3592270e49909120354b051ea8bd
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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