Hydrochloric Acid → HCID 20511303, compound

HRID 614603Notes

Reaction equation

HRID 614603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH:19](OCC)[O:20]CC)[NH:11][CH:10]=[C:9]1[C:26]([O:28][CH3:29])=[O:27].Cl>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH:19]=[O:20])[NH:11][CH:10]=[C:9]1[C:26]([O:28][CH3:29])=[O:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70071948HCID 70071948, compound

Product 1

HCID 20511303HCID 20511303, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of a yellow oil (360 mg) of methyl 4-(2-chlorophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate in acetone (10 ml) was added 6N hydrochloric acid (0.3 ml) and the resultant mixture was stirred for 1.5 hours at room temperaature, and the acetone was removed. Water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried and concentrated. The resultant orange oil (0.26 g) was crystallized and the crystals were washed with n-hexane to give yellowish-orange powder (80.7 mg) of methyl 4-(2-chlorophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3-carboxylate.

Workup

  1. customthe acetone was removed
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe resultant orange oil (0.26 g) was crystallized
  8. washthe crystals were washed with n-hexane

Sources & evidence

ORD record
ord-431f42f1b3664b92bd2c69a3c5dfa472
Source dataset
uspto-grants-1979_03
Patent number
US04145432

Reaction notes

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