3-Iodobenzaldehyde → HCID 68120953, compound

HRID 918443Notes

Reaction equation

HRID 918443 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH2:10]([O:12][C:13](=[O:21])[CH2:14][C:15]([CH2:17][O:18][CH2:19][CH3:20])=O)[CH3:11].[CH2:22]([O:24][C:25](=[O:30])/[CH:26]=[C:27](\[NH2:29])/[CH3:28])[CH3:23]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([I:1])[CH:3]=2)[C:26]([C:25]([O:24][CH2:22][CH3:23])=[O:30])=[C:27]([CH3:28])[NH:29][C:15]=1[CH2:17][O:18][CH2:19][CH3:20])=[O:21])[CH3:11]

Participants

5

Reactant 3

HCID 2526103-IodobenzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 3016245Ethyl 4-ethoxy-3-oxobutyrate

Product 1

HCID 68120953HCID 68120953, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.8 g of 3-iodobenzaldehyde, 4.4 g of γ-ethoxyacetoacetic acid ethyl ester and 3.3 g of β-aminocrotonic acid ethyl ester in 30 ml of ethanol is heated to the boil overnight and is then cooled. After cooling, 2-ethoxymethyl-6-methyl-4-(3'-iodophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is obtained in a yield of 60% of theory in the form of light yellow crystals which melt at 124°C.

Workup

  1. temperatureis then cooled
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-dbf1825e49bb419aa0ad74e354b50513
Source dataset
uspto-grants-1976_07
Patent number
US03971796

Reaction notes

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