Ammonia → HCID 70416078, compound

HRID 569172Notes

Reaction equation

HRID 569172 reaction equation
[C:1]([O:7][CH2:8][C:9]([CH3:30])([CH3:29])[CH2:10][O:11][CH2:12]/[C:13](/[CH3:28])=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][CH:16]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH3:31]>CC(O)C>[NH2:31]/[C:3](/[CH3:5])=[CH:2]\[C:1]([O:7][CH2:8][C:9]([CH3:30])([CH3:29])[CH2:10][O:11][CH2:12]/[C:13](/[CH3:28])=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][CH:16]=1)=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14010660HCID 14010660, compound

Product 1

HCID 70416078HCID 70416078, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 9.5 ml of 2-propanol was dissolved 1.9 g of 3-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]-2,2-dimethylpropyl acetoacetate, and an ammonia gas was blown thereinto with ice-cooling for 30 minutes, after which the resulting mixture was subjected to reaction at room temperature for one day. Subsequently, the solvent was removed by distillation under reduced pressure to obtain oily 3-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]-2,2-dimethylpropyl 3-aminocrotonate. This oily product and 1.15 g of methyl 2-(3-nitrobenzylidene)acetoacetate were dissolved in 9.5 ml of 2-propanol, and the resulting solution was subjected to reaction under reflux for 3 hours. Subsequently, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Merck Silica Gel, 70-230 mesh, eluant: n-hexane:acetone (2:1 by volume)] to obtain 2.34 g (yield 79.0%) of yellow and oily 3-[3-[ (E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]-2,2-dimethylpropyl]5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. temperaturewith ice-cooling for 30 minutes
  2. customafter which the resulting mixture was subjected to reaction at room temperature for one day
  3. customSubsequently, the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-dd9b70b601c5448997f06e30f6e45354
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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