Dimethylformamide → 4-Amino-3-(trifluoromethyl)benzonitrile

HRID 2358386Notes

Reaction equation

HRID 2358386 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[CH3:13][N:14](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]#[N:14])=[CH:3][C:4]=1[C:9]([F:12])([F:11])[F:10]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 32894324-Iodo-2-(trifluoromethyl)aniline

Product 1

HCID 27794884-Amino-3-(trifluoromethyl)benzonitrileYield 99.28%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 178418397HCID 178418397, compoundCatalyst2×

Procedure

4-Iodo-2-trifluoromethylphenylamine (50 mg, 0.17 mmol), Zn(CN)2 (0.88 eq, 0.15 mmol, 18.00 mg), and Pd(PPh3)4 (0.1 eq, 0.02 mmol, 19.64 mg) were added in DMF. Zn(CN)2 (0.88 eq, 0.15 mmol, 18.00 mg) and Pd(PPh3)4 (0.1 eq, 0.02 mmol, 19.64 mg) were added into the reaction mixture. The reaction mixture was stirred for 12 hr. The reaction mixture was purified according to step 1 of Example 8 to give a title product as a yellow solid (31.4 mg, 99.28%).

Workup

  1. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-6b2ad0d85656467c995735799c585ae7
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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