1,3-Cyclohexanedione → HCID 13533641, compound

HRID 464125Notes

Reaction equation

HRID 464125 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[C:9]1(=[O:16])[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1.[CH2:17]([O:19][C:20](=[O:25])/[CH:21]=[C:22](\[NH2:24])/[CH3:23])[CH3:18]>C(O)C>[CH2:17]([O:19][C:20]([C:21]1[CH:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)[C:10]2[C:9](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]=2[NH:24][C:22]=1[CH3:23])=[O:25])[CH3:18]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 1

HCID 13533641HCID 13533641, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-methyl-imidazole-2-carboxaldehyde (4.9 g, 0.045 mole), 1,3-cyclohexandione (5.8 g, 0.045 mole), and ethyl-3-aminocrotonate (5.04 g, 0.045 mole), in 50 mL of absolute ethanol was refluxed for 24 hours. The reaction mixture was cooled and the separated solid was filtered and recrystallized from a hexane-ethylacetate (1:1) mixture to afford 5.2 g (37% yield) of the title compound, m.p. 271°-272° C.; MS, m/e 315 (M+); NMR (CDCl3) δ 1.0 (t, 3 H, CCH 3), 1.5-2.4 (m, 6 H, cyclohexanone), 2.5 (s, 3 H, =CCH3), 3.9-4.1 (q, 2 H, CH2C), 4.0 (s, 3 H, NCH3), 5.2 (s, 1 H, dihydropyridine-H), 6.3 (d, 1 H, imidazole-H), 6.5 (d, 1 H, imidazole-H) and 9.5 (s, 1 H, NH).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe separated solid was filtered
  3. customrecrystallized from a hexane-ethylacetate (1:1) mixture

Sources & evidence

ORD record
ord-8aecddd7f08540e0a4f40084362f190e
Source dataset
uspto-grants-1985_10
Patent number
US04546186

Reaction notes

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