Triethylamine → 4-Amino-3-fluorobenzonitrile

HRID 394795Notes

Reaction equation

HRID 394795 reaction equation
CCOC(C)=O.[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[C:11]([NH2:13])=O.CCN(CC)CC>C(Cl)Cl>[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[NH2:17])[C:11]#[N:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 114239673-Fluoro-4-nitrobenzamide

Product 1

HCID 27564314-Amino-3-fluorobenzonitrileYield 114.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. EtOAc (150 mL) solution of 3-fluoro-4-nitrobenzamide (4.85 g, 26.4 mmol) and Et3N (5.34 g, 52.8 mmol) was added dropwise a CH2Cl2 (50 mL) solution of 1,1,1-trichloroacetyl chloride (5.28 g, 29.04 mmol). The reaction was complete in 2 h (TLC, 1:1 hexane:EtOAc), then it was washed with 1N HCl, dried (MgSO4) and evaporated to give 4.1 g of the corresponding nitrile.

Workup

  1. customTo a 0° C
  2. wash(TLC, 1:1 hexane:EtOAc), then it was washed with 1N HCl
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-bb4c26d451f645b1a14d04531fcc5c55
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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