Ammonia → HCID 20238663, compound

HRID 364965Notes

Reaction equation

HRID 364965 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[F:12][CH2:13][C:14](=O)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[NH3:22]>C(O)C>[F:12][CH2:13][C:14]1[NH:22][C:14]([CH2:13][F:12])=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 74493-NitrobenzaldehydeHCID 9744Acetoacetic acid, 4-fluoro-, ethyl ester

Product 1

HCID 20238663HCID 20238663, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Nitrobenzaldehyde (1.51 g, 10 mmoles), ethyl 4-fluoro-3-oxo-butanoate (3 g, 20 mmoles) and aqueous ammonia (1.1 ml, d=0.88) in ethanol (15 ml) were heated at reflux for 14 hours more aqueous ammonia (0.55 ml) was added after 6 hours. The solvent was removed in vacuo and the residue was chromatographed on silica eluting with ether/petroleum ether (60°-80°) mixtures and the product obtained was recrystallised from 2-propanol to give the title compound as yellow crystals (0.4 g) mp 113°-4°.

Workup

  1. additionwas added after 6 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was chromatographed on silica eluting with ether/petroleum ether (60°-80°) mixtures
  4. customthe product obtained
  5. customwas recrystallised from 2-propanol

Sources & evidence

ORD record
ord-9a9a41ccbdf14090ae765130391ee5f0
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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