Methyl 2-amino-5-bromobenzoate → Methyl 2-amino-5-cyanobenzoate

HRID 321996Notes

Reaction equation

HRID 321996 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:5]=1[NH2:11].[Cu][C:14]#[N:15]>CN1CCCC1=O.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:14]#[N:15])[CH:7]=[CH:6][C:5]=1[NH2:11]

Participants

5

Reactant 2

HCID 736224Methyl 2-amino-5-bromobenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 10058039Methyl 2-amino-5-cyanobenzoateYield 28.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Amino-5-bromobenzoic acid methyl ester (4.6 g, 20 mmol) and copper (I) cyanide (3.6 g, 40 mmol) were heated at 200° C. in N-methylpyrrolidinone (20 ml) for 4 h. After cooling to room temperature, the solution was diluted with water, extracted with ethyl acetate, the aqueous extract acidified with 2N hydrochloric acid and filtered. The organic layer was separated, dried over magnesium sulphate and evaporated. The residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane to yield the title compound as a colourless oil (1.0 g). MS (+El) m/z 176 [M+].

Workup

  1. extractionextracted with ethyl acetate
  2. extractionthe aqueous extract
  3. filtrationfiltered
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7fdd55d8aa5143d290d16343d4c48335
Source dataset
uspto-grants-2001_04
Patent number
US06211189B1

Reaction notes

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