3-Fluoro-p-anisaldehyde → HCID 68120912, compound

HRID 329276Notes

Reaction equation

HRID 329276 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[CH2:12]([O:14][C:15](=[O:23])[CH2:16][C:17]([CH2:19][O:20][CH2:21][CH3:22])=O)[CH3:13].[CH2:24]([O:26][C:27](=[O:32])/[CH:28]=[C:29](\[NH2:31])/[CH3:30])[CH3:25]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[CH:5]([C:4]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([F:1])[CH:3]=2)[C:28]([C:27]([O:26][CH2:24][CH3:25])=[O:32])=[C:29]([CH3:30])[NH:31][C:17]=1[CH2:19][O:20][CH2:21][CH3:22])=[O:23])[CH3:13]

Participants

5

Reactant 3

HCID 676963-Fluoro-p-anisaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 3016245Ethyl 4-ethoxy-3-oxobutyrate

Product 1

HCID 68120912HCID 68120912, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.4 g of 3-fluoro-4-methoxybenzaldehyde, 17.4 g of γ-ethoxyacetoacetic acid ethyl ester and 13 g of β-aminocrotonic acid ethyl ester in 80 ml of ethanol are heated to the boil overnight, the mixture is cooled, and after filtration and rinsing with cold ethanol, 2-ethoxymethyl-6-methyl-4-(3'-fluoro-4'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is obtained in 35% yield of theory, in the form of white crystals of melting point 120° C.

Workup

  1. temperaturethe mixture is cooled
  2. filtrationafter filtration
  3. washrinsing with cold ethanol

Sources & evidence

ORD record
ord-1b340e49846f40738b69a682bb89651c
Source dataset
uspto-grants-1977_04
Patent number
US04020178

Reaction notes

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