Ammonia → 4-Amino-2-fluoro-5-nitrobenzonitrile

HRID 1808882Notes

Reaction equation

HRID 1808882 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].[NH3:14]>C(O)C>[NH2:14][C:8]1[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 118197152,4-Difluoro-5-nitrobenzonitrile

Product 1

HCID 104197934-Amino-2-fluoro-5-nitrobenzonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2,4-difluoro-5-nitrobenzonitrile (2 g, 10.86 mmol, prepared as described in: [Ohmori, J.; Sakamoto, S. et. al. J. Med. Chem., 1994, 37(4), 467-475.]) in ethanol (1.25 ml) was added ammonia (6.25 mL, 10.86 mmol) at r.t. The mixture was stirred overnight. Filtered to collect the precipitate, washed w/H2O (3×). The solid was dried in vacuo for 24 hrs to afford 1.9 g of 4-amino-2-fluoro-5-nitrobenzonitrile (1.8 g, 9.44 mmol, 87% yield), which was used in the next reaction without further purification. 1H-NMR (CD3OD, 500 MHz): δ 8.55 (1H, s), 6.82 (1H, s). m/e (M+H): 182.1.

Workup

  1. filtrationFiltered
  2. customto collect the precipitate
  3. washwashed w/H2O (3×)
  4. customThe solid was dried in vacuo for 24 hrs

Sources & evidence

ORD record
ord-635063bd2d904fd3a5f72c5e7a246c64
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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