Isopropanol → HCID 14098295, compound

HRID 648457Notes

Reaction equation

HRID 648457 reaction equation
O1[C:5](=O)[CH:4]=[NH+:3][N-]1.[CH:7]([C:9]1[C:13](=O)O[N-][N+:10]=1[CH3:15])=O.[NH2:16]/[C:17](/[CH3:23])=[CH:18]\[C:19]([O:21][CH3:22])=[O:20].[C:24]([O:30][CH3:31])(=[O:29])[CH2:25][C:26]([CH3:28])=O.[CH:32](O)(C)[CH3:33]>>[CH3:23][C:17]1[NH:16][C:26]([CH3:28])=[C:25]([C:24]([O:30][CH3:31])=[O:29])[CH:7]([C:9]2[N:10]=[CH:15][N:3]3[CH:4]=[CH:5][CH:33]=[CH:32][C:13]=23)[C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 7757Methyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 178482033HCID 178482033, compound

Product 1

HCID 14098295HCID 14098295, compound

Procedure

To 1.02 g (7 mmol) 1-formylimidazo[1,5-a]pyridine (1) in 20 ml isopropanol was added 0.81 g methyl 3-aminocrotonate and 0.81 g (7 mmol) methyl acetoacetate and the resulting solution refluxed for 14 hours. The cooled reaction mixture was filtered to give a yellow solid which was recrystallized from CH3OH to afford pure (2), m.p. 265°-267° (dec).

Workup

  1. temperaturethe resulting solution refluxed for 14 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customto give a yellow solid which
  5. customwas recrystallized from CH3OH

Sources & evidence

ORD record
ord-36f323b970854b62bf0b746e96bb7e51
Source dataset
uspto-grants-1988_04
Patent number
US04735956

Reaction notes

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