Sodium Bicarbonate → HCID 12900709, compound

HRID 2166566Notes

Reaction equation

HRID 2166566 reaction equation
O.Cl.[CH2:3]([N:10]1[CH2:15][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:13][C:12](=[O:26])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>C(O)C>[CH2:3]([N:10]1[CH2:11][CH:12]([OH:26])[CH:13]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=2)[CH2:15]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 204998051-benzyl-1,6-dihydro-5-(p-trifluoromethylphenyl)-3-(2H)pyridone hydrochloride hydrate

Product 1

HCID 12900709HCID 12900709, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-benzyl-1,6-dihydro-5-(p-trifluoromethylphenyl)-3-(2H)pyridone hydrochloride hydrate (11.6 g) in ethanol (250 ml) was treated with sodium bicarbonate (2 g) followed by sodium borohydride (1.5 g). After 2 hours the solvents were removed under reduced pressure and the residue partitioned between water (100 ml) and ether (400 ml). The organic phase was dried and the solvent removed under reduced pressure. Recrystallisation of the residue from cyclohexane gave the title compound (7.3 g), m.p. 88°-90°.

Workup

  1. customAfter 2 hours the solvents were removed under reduced pressure
  2. customthe residue partitioned between water (100 ml) and ether (400 ml)
  3. customThe organic phase was dried
  4. customthe solvent removed under reduced pressure
  5. customRecrystallisation of the residue from cyclohexane

Sources & evidence

ORD record
ord-cca9298d0c3d43979848e04a79225b69
Source dataset
uspto-grants-1983_06
Patent number
US04387230

Reaction notes

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