Water → HCID 19608243, compound

HRID 745048Notes

Reaction equation

HRID 745048 reaction equation
[CH:1]([C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[CH:27]=[CH:26][C:13]([C:14]([N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:27]=[CH:26][C:13]([C:14]([N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:12][CH:11]=2)=[O:8])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19608019HCID 19608019, compound

Product 1

HCID 19608243HCID 19608243, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[4-(4-formylbenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.3 g) in methanol (10 ml) is added gradually sodium borohydride (59 mg) under ice-cooling and the mixture is stirred at room temperature for 2 hours. Water is added to the mixture and the solvent is distilled off under reduced pressure. The resulting residue is extracted with dichloromenhane, washed with water, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane methanol=50: 1), and recrystallized from methanol to give 1-[4-(4-hydroxymethylbenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (165 mg) as white powder, m.p. 224.5°-225.5° C.

Workup

  1. temperaturecooling
  2. distillationthe solvent is distilled off under reduced pressure
  3. extractionThe resulting residue is extracted with dichloromenhane
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane methanol=50: 1)
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b306a7accb3f4adfb0f81a65a3720570
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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