Ammonia → 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethyl 3-aminocrotonate
Reaction equation
[C:1]([O:7][CH2:8][CH2:9][O:10][CH2:11]/[C:12](/[CH3:27])=[CH:13]/[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][CH:15]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH3:28].CCCCCC>CC(O)C>[NH2:28]/[C:3](/[CH3:5])=[CH:2]\[C:1]([O:7][CH2:8][CH2:9][O:10][CH2:11]/[C:12](/[CH3:27])=[CH:13]/[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][CH:15]=1)=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In 8 ml of 2-propanol was dissolved 2.0 g of 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethyl acetoacetate, and ammonia gas was introduced into the resulting solution for 2 hours with ice-cooling. And, the solution was subjected to reaction at room temperature for 15 hours. Subsequently, the solvent was removed by distillation under reduced pressure, and to the residue thus obtained were added 2 ml of 2-propanol and 8 ml of n-hexane, after which the resulting mixture was stirred. The crystals thus precipitated were collected by filtration to obtain 1.6 g (yield 80.2%) of 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethyl 3-aminocrotonate.
Workup
- additionwas introduced into the resulting solution for 2 hours with ice-
- temperaturecooling
- customAnd, the solution was subjected to reaction at room temperature for 15 hours
- customSubsequently, the solvent was removed by distillation under reduced pressure
- customto the residue thus obtained
- customThe crystals thus precipitated
- filtrationwere collected by filtration
Sources & evidence
- ORD record
- ord-912bab0a6b064429be1d2bce478246cc
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04731370
Reaction notes
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