Ammonia → Ethyl 4-amino-2-fluoro-5-nitrobenzoate

HRID 1410230Notes

Reaction equation

HRID 1410230 reaction equation
[F:1][C:2]1[CH:12]=[C:11](F)[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH3:17].O>C1COCC1>[NH2:17][C:11]1[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([F:1])[CH:12]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 962WaterHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoate

Product 1

HCID 59529828Ethyl 4-amino-2-fluoro-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of ethyl 2,4-difluoro-5-nitrobenzoate (5.00 g; 21.6 mmol) (see Example 59 (d)) in THF (100 mL) was treated with NH3 in THF (2.7 mL; 8 M; 21.6 mmol) at 0° C. and the mixture was stirred over night. Another portion of NH3 in THF (1.0 mL; 8M; 8 mmol) was added and the mixture stirred over night. Water (100 mL) was added and the mixture was concentrated. The precipitate was filtered off and dried to give the sub-title compound.

Workup

  1. stirringthe mixture stirred over night
  2. concentrationthe mixture was concentrated
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-53bb9b409d944c3eb0194c749cb672c7
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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