HCID 318534, compound → HCID 14950493, compound

HRID 1769074Notes

Reaction equation

HRID 1769074 reaction equation
[NH2:1][C:2]([CH3:12])=[CH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].O[C:14](=[C:17]1C(=O)OC(C)(C)[O:19][C:18]1=O)[CH2:15][CH3:16]>>[C:4]([C:3]1[C:18](=[O:19])[CH:17]=[C:14]([CH2:15][CH3:16])[NH:1][C:2]=1[CH3:12])(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 318534HCID 318534, compoundHCID 547061775-(1-Hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 14950493HCID 14950493, compoundYield 27.6%

Conditions

Temperature
120 °C

Procedure

A mixture of 3-amino-1-phenyl-2-buten-1-one (2.3 g) and 5-(1-hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (4.0 g) was heated at 120° C. for 1 hour. The mixture was cooled to ambient temperature and the residue was purified by flash chromatography eluting with dichloromethane/methanol (19:1 v/v) to give 3-benzoyl-1,4-dihydro-6-ethyl-2-methyl-4-oxopyridine (0.95 g) as a solid, m.p. 203° C.; NMR (d6 -DMSO): 1.2(t, 3H), 2.07(s, 3H), 2.5(q, 2H), 5.96(s, 1H), 7.44-7.50(m, 2H), 7.57-7.60(m, 1H), 7.72-7.76(m, 2H), 11.3(broad s, 1H); mass spectrum (chemical ionisation, ammonia): 242(M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe residue was purified by flash chromatography
  3. washeluting with dichloromethane/methanol (19:1 v/v)

Sources & evidence

ORD record
ord-8693beba4eb84884865edd288139f588
Source dataset
uspto-grants-1995_01
Patent number
US05380730

Reaction notes

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