Ammonia → HCID 19009993, compound

HRID 2254137Notes

Reaction equation

HRID 2254137 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:16])[CH2:12][C:13]([CH3:15])=O.[NH3:25]>CO>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:12]([C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[C:13]([CH3:15])[NH:25][C:13]([CH3:15])=[C:12]1[C:11]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 357452,3-DichlorobenzaldehydeHCID 142266Benzyl acetoacetate

Product 1

HCID 19009993HCID 19009993, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

In a 7% ammonia solution in methanol were dissolved 2.6 g of 2,3-dichlorobenzaldehyde and 5.8 g of benzyl acetoacetate, and the solution was stirred in a closed tube at 90° C. for 10 hours, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4) to obtain 4.8 g (yield: 30%) of dibenzyl 4-(2,3-dichlorophenyl) -1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate as a yellow crystal.

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-91e1faf92b4e45aea28d6ce2f362115b
Source dataset
uspto-grants-1993_08
Patent number
US05234821

Reaction notes

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