Hydrochloric Acid → HCID 13469489, compound

HRID 1248703Notes

Reaction equation

HRID 1248703 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:32]=[O:33])=[C:5]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])[C:7]=1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[BH4-].[Na+].O.Cl>C(O)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:32][OH:33])=[C:5]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])[C:7]=1[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 86736422HCID 86736422, compound

Product 1

HCID 13469489HCID 13469489, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspended solution of benzyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3-carboxylate (1.2 g) in ethanol (20 ml) was added sodium borohydride (60.6 mg) under ice-cooling and stirred, and further stirred for an hour at 0° C. and another an hour at 3° C. The reaction mixture was added with water and the resultant mixture was adjusted to pH 6 to 7 with 2N hydrochloric acid, and the solvent was distilled off. The residue was extracted with ethyl acetate and washed with water and dried. After removal of the solvent, the resultant oil (1.3 g) was purified by column chromatography on silica gel with an eluent (a mixture of ten parts of benzene and one part of ethyl acetate by volume) to give an oil which was immediately crystallized. The resultant crystals were recrystallized from a mixture of diethyl ether and n-hexane and dissolved in benzene. The benzene solution was subjected to azeotropic process five times to give pure crystals of benzyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 51° to 57° C.

Workup

  1. temperaturecooling
  2. stirringfurther stirred for an hour at 0° C. and another an hour at 3° C
  3. distillationthe solvent was distilled off
  4. extractionThe residue was extracted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. customAfter removal of the solvent
  8. customthe resultant oil (1.3 g) was purified by column chromatography on silica gel with an eluent (
  9. additiona mixture of ten parts of benzene and one part of ethyl acetate by volume)
  10. customto give an oil which
  11. customwas immediately crystallized
  12. customThe resultant crystals were recrystallized from a mixture of diethyl ether and n-hexane
  13. dissolutiondissolved in benzene

Sources & evidence

ORD record
ord-041f958172764b7089f1fd7c06db0c65
Source dataset
uspto-grants-1985_06
Patent number
US04525478

Reaction notes

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