Hydrochloric Acid → HCID 13388341, compound

HRID 1164611Notes

Reaction equation

HRID 1164611 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:28]=[O:29])=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[BH4-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:28][OH:29])=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:20])[F:21])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15737327HCID 15737327, compound

Product 1

HCID 13388341HCID 13388341, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of diethyl 2-methyl-4-(2-trifluoromethylphenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (1.0 g) in ethanol (20 ml) was gradually added sodium borohydride (92 mg) under stirring and ice-cooling and the resultant mixture was further stirred for 25 minutes. The resultant mixture was adjusted with 0.1 N hydrochloric acid to pH 4 to 5. The ethanol was removed under reduced pressure without heating so much, and water was added to the residue to give crystals. The crystals were collected by filtration to give crude crystals (1.2 g). These were recrystallized from a mixture of diethyl ether and n-hexane to give pure crystals of diethyl 2-methyl-4-(2-trifluoromethylphenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate, m.p. 147° to 148.5° C.

Workup

  1. temperatureice-cooling
  2. customThe ethanol was removed under reduced pressure
  3. temperaturewithout heating so much
  4. additionwater was added to the residue
  5. customto give crystals
  6. filtrationThe crystals were collected by filtration
  7. customto give crude crystals (1.2 g)
  8. customThese were recrystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-5f249f1138bf452294d2c5f6ce9830c0
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

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