Water → HCID 59529818, compound

HRID 410096Notes

Reaction equation

HRID 410096 reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[CH:14]=[C:13](F)[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7].O>C1COCC1>[F:3][C:4]1[CH:14]=[C:13]([NH:2][CH3:1])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 6329Methylamine2×HCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoate

Product 1

HCID 59529818HCID 59529818, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 2M solution of MeNH2 in THF (21.6 mL; 43.3 mmol) is added dropwise to a solution of ethyl 2,4-difluoro-5-nitrobenzoate (5.0 g; 21.6 mmol) in THF (70 mL) at −5° C. The mixture is left overnight at rt whereafter an additional portion of 2M MeNH2 in THF (10.0 mL; 2 M; 21.6 mmol) is added at 0° C. After 3 h at rt, water is added and the mixture is concentrated. The resulting precipitate is filtered off and dried to give the sub-title compound. Yield: 5.0 g (96%).

Workup

  1. additionis added at 0° C
  2. concentrationthe mixture is concentrated
  3. filtrationThe resulting precipitate is filtered off
  4. customdried

Sources & evidence

ORD record
ord-9012f8036f42440db944c631a732715a
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

Loading…