Ammonia → Methyl 5-amino-2-cyanobenzoate

HRID 1888367Notes

Reaction equation

HRID 1888367 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1Br.[C:13]([Cu])#[N:14].O.N>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 245495Methyl 5-amino-2-bromobenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 53419719Methyl 5-amino-2-cyanobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

The mixture of 5-amino-2-bromobenzoic acid methyl ester (14.27 g, 62.0 mmol) and CuCN (6.11 g, 68.2 mmol) in DMF (130 ml) was heated at 150° C. for 1 h 10 min under nitrogen atmosphere. The mixture was cooled to 70° C. and poured into the mixture of water (250 ml) and 12.5% NH3 (500 ml). The product was extracted into ethyl acetate (3×250 ml). The organic phase was washed several times with 12.5% NH3 and water, dried over Na2SO4 and concentrated under vacuum.

Workup

  1. temperatureThe mixture was cooled to 70° C.
  2. extractionThe product was extracted into ethyl acetate (3×250 ml)
  3. washThe organic phase was washed several times with 12.5% NH3 and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f4a1ca1586f34ff38ef1527bc7f2ffa2
Source dataset
uspto-grants-2013_08
Patent number
US08501814B2

Reaction notes

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