Methyl 3-aminocrotonate → 3-Chloro-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 483202Notes

Reaction equation

HRID 483202 reaction equation
[F:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[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][C:29]([CH3:33])([CH3:32])[CH2:30][Cl:31])(=[O:26])[CH2:22][C:23]([CH3:25])=O>C(O)(C)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]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=2[F:1])[C:22]=1[C:21]([O:27][CH2:28][C:29]([CH3:33])([CH3:32])[CH2:30][Cl:31])=[O:26]

Participants

5

Reactant 3

HCID 643918Methyl 3-aminocrotonateHCID 104873252-Fluoro-3-nitrobenzaldehydeHCID 538143253-Chloro-2,2-dimethylpropyl acetoacetate

Product 1

HCID 704570723-Chloro-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1.70 g of 2-fluoro-3-nitrobenzaldehyde in 10 ml of isopropanol were added 1.15 g of methyl 3-aminocrotonate and 2.10 g of 3-chloro-2,2-dimethylpropyl acetoacetate. The mixture was refluxed for 5 hours. Solvent was distilled off under reduced presoure to leave a residue. The residue was chromatographed on silica gel to give 2.09 g of 3-chloro-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. distillationSolvent was distilled off
  3. customto leave a residue
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-ed74e46f860542a0b6a141ef40c43b2a
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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