Water → HCID 19608243, compound

HRID 1603088Notes

Reaction equation

HRID 1603088 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 dichloromethane, 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 dichloromethane
  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-e3af5fcbe67d4966b74f997afa480470
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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