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

HRID 410088Notes

Reaction equation

HRID 410088 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]>C1COCC1>[F:1][C:2]1[CH:12]=[C:11]([NH2:17])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2,4-difluoro-5-nitro-benzoate (5.0 g, 21 mmol), 5.2 mL conc. NH3 and THF (25 mL) is stirred for 30 min in an ice bath and overnight at rt. The mixture is concentrated and diluted with water. The precipitate is filtered, washed with water and dried at 55° C. to furnish the crude sub-title compound.

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with water
  3. filtrationThe precipitate is filtered
  4. washwashed with water
  5. customdried at 55° C.

Sources & evidence

ORD record
ord-5adf13836dd14585ac25c36bd8c0db63
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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