Hydrochloric Acid → HCID 13469471, compound

HRID 1164612Notes

Reaction equation

HRID 1164612 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:26]=[O:27])=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[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]([CH2:26][OH:27])=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 13469466HCID 13469466, compound

Product 1

HCID 13469471HCID 13469471, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of diethyl 2-methyl-4-(2-methoxyphenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (1.1320 g) in ethanol (30 ml) was gradually added sodium borohydride (114 mg) under stirring and the resultant mixture was further stirred at room temperature for an hour. The resultant mixture was acidified with dilute hydrochloric acid. After removing ethanol from the mixture, water was added to the residue to solidify. The solid was collected by filtration, dried and washed with diethyl ether. The diethyl ether washings were concentrated to the volume of about 10 ml and stood at room temperature to give pale yellowish granules (372.5 mg) of diethyl 2-methyl-4-(2-methoxyphenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate, m.p. 125° to 126° C.

Workup

  1. customAfter removing ethanol from the mixture, water
  2. additionwas added to the residue
  3. filtrationThe solid was collected by filtration
  4. customdried
  5. washwashed with diethyl ether
  6. concentrationThe diethyl ether washings were concentrated to the volume of about 10 ml
  7. customstood at room temperature

Sources & evidence

ORD record
ord-3bf6496a5398426fb0447c675dbe7321
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

Loading…