Ammonia → NSC512750

HRID 2232378Notes

Reaction equation

[C:1]1([NH:7][C:8](=[O:13])[CH2:9][C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:14]>>[C:1]1([NH:7][C:8](=[O:13])/[CH:9]=[C:10](\[NH2:14])/[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 222Ammonia

HCID 7592Acetoacetanilide

Product 1

HCID 5408087NSC512750

Procedure

N-Phenyl-3-ketobutanamide (0.35 g, 2.0 mmole) was dissolved in ethanolic ammonia (15 ml, 0.105M) and stirred overnight at room temperature. The solution was evaporated to yield N-phenyl-3-aminocrotonamide which was used directly. The crude residue was taken up in ethanol (30 ml) and 2-chlorobenzaldehyde (0.28 g, 2 mmole) and methyl 4-[2-(2,4,5-trimethylimidazol-1-yl)ethoxy]-3-ketobutanoate (0.53 g, 2 mmole) were added. The mixture was heated at reflux for 8 hours then cooled and the solution evaporated to dryness under reduced pressure. The residue was chromatographed on silica eluting with ethyl acetate containing an increasing proportion of up to 10% diethylamine. The fractions containing the product were combined and evaporated to yield the title compound (0.56 g, 51%). m.p. 135°-140° C. Found: C, 65.06; H, 6.14; N, 9.86. C30H33ClN4O4.1/2H2O requires C, 65.09; H, 6.10; N, 10.12%.

Workup

customThe solution was evaporated

Sources & evidence

ORD record: ord-f0c2d6a3e4fe4bfb9f94f16b84346081
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788205

Reaction notes

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