Dimethylformamide → 2-amino-5-cyano-N-methylbenzamide

HRID 511370Notes

Reaction equation

HRID 511370 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9](Br)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:13]#[N:14])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 509995112-Amino-5-bromo-N-methylbenzamide

Product 1

HCID 672549392-amino-5-cyano-N-methylbenzamideYield 48%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 2-Amino-5-bromo-N-methylbenzamide (100.0 mg, 0.4365 mmol), zinc cyanide (51.26 mg, 0.4365 mmol), Pd(PPh3)4 (75.67 mg, 0.06548 mmol) in DMF (1.5 mL) was flushed with nitrogen and irradiated in a microwave reactor at 150° C. for 5 minutes. The reaction mixture was poured into water and extracted by ethyl acetate. The combined organic layers were washed with water and brine, concentrated in vacuo and purified on an ISCO Combiflash unit to isolate the desired product (37.0 mg, 48% yield).

Workup

  1. customwas flushed with nitrogen
  2. customirradiated in a microwave reactor at 150° C. for 5 minutes
  3. additionThe reaction mixture was poured into water
  4. extractionextracted by ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. concentrationconcentrated in vacuo
  7. custompurified on an ISCO Combiflash unit

Sources & evidence

ORD record
ord-e3406c46932248908dae876106ee45b4
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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