Acetic Acid → Brefonalol

HRID 1193494Notes

Reaction equation

HRID 1193494 reaction equation
O[CH:2](O)[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)=[O:4].[CH3:17][C:18]([CH3:28])([NH2:27])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C.CN(C)C=O>[OH:4][CH:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH2:2][NH:27][C:18]([CH3:28])([CH3:17])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 12851223HCID 12851223, compoundHCID 13592681HCID 13592681, compound

Product 1

HCID 65880Brefonalol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.4 g (0.006 mole) of 3,4-dihydro-6-(alpha,alpha-dihydroxy-acetyl)-quinolin-2-(1H)-one and 1.37 g (0.008 mole) of 1,1-dimethyl-3-phenyl-propanamine in 60 ml of ethanol and 30 ml of dimethylformamide is heated to 80° C. for 2 hours and, after cooling to room temperature, about 1.5 g of sodium borohydride are gradually added. After 2 hours, the mixture is acidified with acetic acid and the solvent is evaporated off in vacuo. After being rendered alkaline with 2N sodium hydroxide solution, the residue is extracted with methylene chloride. The residue of the organic phase is purified by column chromatography on silica gel (CHCl3 /MeOH 93/7).

Workup

  1. customthe solvent is evaporated off in vacuo
  2. extractionthe residue is extracted with methylene chloride
  3. customThe residue of the organic phase is purified by column chromatography on silica gel (CHCl3 /MeOH 93/7)

Sources & evidence

ORD record
ord-8d7a47d95da8481eb22383727fb6df18
Source dataset
uspto-grants-1989_03
Patent number
US04810712

Reaction notes

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