Methanol → HCID 19607986, compound

HRID 745054Notes

Reaction equation

HRID 745054 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12](=[O:30])[C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)=[CH:15][CH:14]=2)[CH2:4][CH2:3]1.O1CCCC1.CO.[BH4-].[Na+]>O>[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12](=[O:30])[C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)=[CH:17][CH:18]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 18919728HCID 18919728, compound

Product 1

HCID 19607986HCID 19607986, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-oxo-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline(0.7 g) are added tetrahyrdofuran (10 ml) and methanol (10 ml). To the mixture is added sodium borohydride (0.1 g) in portions and the mixture is stirred at room temperature for 1 hour. Water is added to the reaction mixture and the mixture is extracted with dichloromethane. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane→dichloromethane:methanol=20:1), and recrystallized from ethanol to give 4-hydroxy-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.4 g) as white powder, m.p. 215°-217° C.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. concentrationThe solvent is concentrated
  3. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane→dichloromethane:methanol=20:1)
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-88fa5259a3c94fd1884ce0e35cc5d4b8
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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