Acetic Acid → 2-Aminobenzhydrol

HRID 1377696

Reaction equation

HRID 1377696 reaction equation
C(O)(=O)C.[BH4-].[Na+].[H][H].[NH2:9][C:10]1[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].C(=O)(O)[O-].[Na+]>C1COCC1.O.CCCCCC.CCOC(C)=O>[NH2:9][C:10]1[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=1[CH:12]([OH:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 760802-AminobenzophenoneHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 2708102-Aminobenzhydrol

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (2.28 mL, 2.4 g, 40.4 mmol) was added slowly to sodium borohydride (0.76 g, 20.2 mmol) in THF (20 mL) stirred in an ice bath. The mixture was stirred in the cold until hydrogen evolution had ceased. 2-Aminobenzophenone (2.0 g, 10.1 mmol) was added as the solid. The mixtuire was stirred under nitrogen at ambient temperature for 20 hours, after which time, TLC assay (silica gel, 1:9 EtOAc:hexane) indicated reaction was complete. The reaction mixture was treated with water (40 mL), then neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layers were combined, dired over sodium sulfate, filtered, and evaporated to dryness in vacuo to give 2-aminobenzhydrol.

Workup

  1. stirringThe mixtuire was stirred under nitrogen at ambient temperature for 20 hours
  2. customreaction
  3. extractionextracted with ethyl acetate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-1b677fc41a5343fbbd79c4676be40793
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Linked notes

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