Isopropanol → HCID 14098294, compound

HRID 648456Notes

Reaction equation

HRID 648456 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:5]([C:4]2[N:10]3[CH:15]=[CH:32][CH:33]=[CH:13][C:9]3=[CH:7][N:3]=2)[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 14098294HCID 14098294, compound

Procedure

To 0.58 g (4 mmol) 3-formylimidazo[1,5-a]pyridine (1) in 15 ml isopropanol was added 0.46 g (4 mmol) methyl 3-aminocrotonate and 0.46 g (4 mmol) methyl acetoacetate and the resulting solution was heated at reflux for 20 hours. The cooled reaction mixture was then filtered to give a yellow solid which was washed with ether and subsequently recrystallized from methanol to give pure (2), m.p. 255°-257° (dec).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 20 hours
  3. customThe cooled reaction mixture
  4. filtrationwas then filtered
  5. customto give a yellow solid which
  6. washwas washed with ether
  7. customsubsequently recrystallized from methanol

Sources & evidence

ORD record
ord-73e3673eaa5e4177bb119b12e5b04603
Source dataset
uspto-grants-1988_04
Patent number
US04735956

Reaction notes

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