p-Nitroacetophenone → HCID 10999672, compound

HRID 13482

Reaction equation

HRID 13482 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1([CH2:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7487p-NitroacetophenoneHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10999672HCID 10999672, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-nitrophenyl)ethan-1-one (1 eq) and phenylmethylamine (1 eq) in methanol was added sodium triacetoxyborohydride (1.2 eq). The resulting mixture was stirred at ambient temperature for 16 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was concentrated and preparative purification yielded [(4-nitrophenyl)ethyl]benzylamine. MS: MH+=256.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. concentrationThe organic layer was concentrated
  4. custompreparative purification

Sources & evidence

ORD record
ord-e35429549cc24636b5bc31c27c701b89
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

Loading…