Hydrochloric Acid → HCID 13469490, compound

HRID 1164618Notes

Reaction equation

HRID 1164618 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]=[O:20])[NH:11][CH:10]=[C:9]1[C:21]([O:23][CH3:24])=[O:22].[BH4-].[Na+].Cl>C(O)C>[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]([CH2:19][OH:20])[NH:11][CH:10]=[C:9]1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20511303HCID 20511303, compound

Product 1

HCID 13469490HCID 13469490, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of powder (329 mg) of methyl 4-(2-chlorophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3-carboxylate in ethanol (10 ml) was added sodium borohydride (25.11 mg) under ice-cooling. After further stirring for 50 minutes, the mixture was adjusted to pH 4 to 5 with dilute hydrochloric acid. After removal of the ethanol, water was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried and the residual crystals (about 280 mg) were dissolved in a mixture of diethyl ether and n-hexane and kept in a refrigerator to give pure crystals (184 mg) of methyl 4-(2-chlorophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 187° to 188° C.

Workup

  1. temperaturecooling
  2. customAfter removal of the ethanol, water
  3. additionwas added to the residue, which
  4. extractionwas extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. customdried
  7. dissolutionthe residual crystals (about 280 mg) were dissolved in a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-5c1732af2ae54a6eba653b0cbfd732ea
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

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