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

HRID 483197Notes

Reaction equation

HRID 483197 reaction equation
[Cl:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=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:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=2[N+:10]([O-:12])=[O:11])[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 117768292-(Benzylmethylamino)ethyl acetoacetateHCID 122489723-CHLORO-2-NITROBENZALDEHYDE

Product 1

HCID 103241642-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-chloro-2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 58.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 556 mg of 3-chloro-2-nitrobenzaldehyde, 362 mg of methyl 3-aminocrotonate and 820 mg of 2-(N-benzyl-N-methylamino)ethyl acetoacetate in 4 ml of 2-propanol was refluxed for 6 hours, and then the solvent was distilled off under reduced pressure. The residue was purified by a method of column chromatography onon silica gel to yield 900 mg of the desired compound (108).

Workup

  1. temperaturewas refluxed for 6 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by a method of column chromatography onon silica gel

Sources & evidence

ORD record
ord-4eb1fbb977484bebbd11e07c08f53323
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

Loading…