3-Nitrobenzaldehyde → HCID 13822787, compound

HRID 986454Notes

Reaction equation

HRID 986454 reaction equation
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH3:28])[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.[NH2:29]/[C:30](/[CH3:38])=[CH:31]\[C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33].[N+:39]([C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[CH:45]=O)([O-:41])=[O:40]>CC(O)C>[CH3:5][C:3]1[NH:29][C:30]([CH3:38])=[C:31]([C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH:45]([C:44]2[CH:47]=[CH:48][CH:49]=[C:42]([N+:39]([O-:41])=[O:40])[CH:43]=2)[C:2]=1[C:1]([O:7][CH2:8][CH2:9][N:10]([CH3:28])[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

HCID 74493-NitrobenzaldehydeHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl esterHCID 13822786HCID 13822786, compound

Product 1

HCID 13822787HCID 13822787, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 4 ml of 2-propanol were dissolved 1.01 g of 2-[N-methyl-N-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyl]amino]ethyl acetoacetate, 0.38 g of isopropyl 3-aminocrotonate and 0.40 g of 3-nitrobenzaldehyde, and the resulting mixture 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 [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (1:1 by volume)] to obtain 1.28 g (yield 71.5%) of yellow, oily 3-[2-[N-methyl-N-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyl]amino]ethyl] 5-isopropyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. customthe resulting mixture was subjected to reaction
  2. temperatureunder reflux for 3 hours
  3. customSubsequently, the solvent was removed by distillation under reduced pressure
  4. customthe residue thus obtained
  5. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (1:1 by volume)]

Sources & evidence

ORD record
ord-094e6bb5896f4e0b905f3b19743af7c0
Source dataset
uspto-grants-1987_12
Patent number
US04713387

Reaction notes

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