Methyl 3-aminocrotonate → 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2-fluoro-5-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 483204Notes

Reaction equation

HRID 483204 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[NH2:13]/[C:14](/[CH3:20])=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].[C:21]([O:27][CH2:28][CH2:29][N:30]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:31])(=[O:26])[CH2:22][C:23]([CH3:25])=O>CC(O)C>[CH3:25][C:23]1[NH:13][C:14]([CH3:20])=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:4]([C:3]2[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=2[F:1])[C:22]=1[C:21]([O:27][CH2:28][CH2:29][N:30]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:31])=[O:26]

Participants

5

Reactant 3

HCID 643918Methyl 3-aminocrotonateHCID 27347702-Fluoro-5-nitrobenzaldehydeHCID 117768292-[Methyl(phenylmethyl)amino]ethyl 3-oxobutanoate

Product 1

HCID 100515692-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2-fluoro-5-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 170 mg of 2-fluoro-5-nitrobenzaldehyde, 126 mg of methyl 3-aminocrotonate and 253 mg of 2-(N-benzyl-N-methylamino)ethyl acetoacetate in 1 ml of 2-propanol was reacted and then purified in the same way as in Example 9 to yield 200 mg of the desired compound (144).

Workup

  1. customwas reacted
  2. custompurified in the same way as in Example 9

Sources & evidence

ORD record
ord-bfcc1d20813543599bc6b2b7414a02ad
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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