Ammonia → HCID 20189398, compound

HRID 1789028Notes

Reaction equation

HRID 1789028 reaction equation
[F:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([C:27](=O)[CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12].[NH3:30]>C(O)C>[F:1][CH2:2][C:3]1[NH:30][C:27]([CH3:28])=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=2)[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 9744Acetoacetic acid, 4-fluoro-, ethyl esterHCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoate

Product 1

HCID 20189398HCID 20189398, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-fluoro-3-oxobutanoate (1.45 g, 10 mmoles), ethyl 2-(3-nitrophenylmethylene)-3-oxobutanoate (2.63 g, 10 mmoles) and aqueous ammonia (1.1 ml, d 0.88) were heated at reflux in ethanol (15 ml) for 6 hours. The solvent was removed in vacuo and the residue purified by chromatography on silica eluting with petroleum ether (60°-80° )/ether mixtures. Recrystallisation from ether/petroleum ether (60°-80° ) gave the title compound (1.1 g) as yellow crystals mp 139°-41°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by chromatography on silica eluting with petroleum ether (60°-80° )/ether mixtures
  3. customRecrystallisation from ether/petroleum ether (60°-80° )

Sources & evidence

ORD record
ord-a5355033654e4c89a95591098884e086
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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