2-Chlorobenzaldehyde → 3-O-ethyl 5-O-methyl 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1589651Notes

Reaction equation

HRID 1589651 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][C:8](=O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N+:2]=[N-:3].N(CCO)=[N+]=[N-].[NH2:22]/[C:23](/[CH3:29])=[CH:24]\[C:25]([O:27][CH3:28])=[O:26].[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=O>CO>[N:1]([CH2:4][CH2:5][O:6][CH2:7][C:8]1[NH:22][C:23]([CH3:29])=[C:24]([C:25]([O:27][CH3:28])=[O:26])[CH:33]([C:32]2[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=2[Cl:30])[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 1231182-AzidoethanolHCID 643918Methyl 3-aminocrotonateHCID 13663141Ethyl 4-(2-azidoethoxy)-3-oxobutanoate

Product 1

HCID 30926063-O-ethyl 5-O-methyl 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylateYield 29.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-(2-azidoethoxy)acetoacetate (46.4 g), prepared from 2-azidoethanol similarly to the method described in Preparation 3, was reacted with methyl 3-aminocrotonate (24.8 g) and 2-chlorobenzaldehyde (30.3 g) in methanol (150 ml) at reflux for 18 hours. After cooling to room temperature, the resulting solid was collected, washed twice with methanol and dried to give the title compound (28 g). The product could be crystallised from methanol, acetone or ethyl acetate. It was used directly.

Workup

  1. customdescribed in Preparation 3
  2. temperatureat reflux for 18 hours
  3. customthe resulting solid was collected
  4. washwashed twice with methanol
  5. customdried

Sources & evidence

ORD record
ord-1898d73dc9674d45a98388837ce7fd60
Source dataset
uspto-grants-1986_02
Patent number
US04572909

Reaction notes

Loading…