Water → 4-Aminobenzophenone

HRID 541165Notes

Reaction equation

HRID 541165 reaction equation
[N:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1)=[N+]=[N-].O>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 962WaterHCID 112183414-Azidobenzophenone

Product 1

HCID 143464-AminobenzophenoneYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

111.6 mg (0.50 mmol) of 4-azidobenzophenone (5), 270 μL (15 mmol) of distilled water and stainless steel balls (50 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 12 hours at 800 rpm (reversed every 30 minutes). After the lapse of 12 hours, 10 mL of ethyl acetate was added to the vessel of the ball mill to provide a solution containing the reaction product, which was then filtered with celite. The operation was repeated 5 times to provide a filtrate, which was then concentrated, thereby providing 87.7 mg (0.45 mmol) of 4-aminobenzophenone (6). The yield was 89%. The reaction is expressed by the following scheme.

Workup

  1. customwas then closed
  2. customfor 12 hours
  3. customto provide a solution
  4. additioncontaining the reaction product, which
  5. filtrationwas then filtered with celite
  6. customto provide a filtrate, which
  7. concentrationwas then concentrated

Sources & evidence

ORD record
ord-dcf774009b3744d9bc932febd8c7ebf1
Source dataset
uspto-grants-2014_10
Patent number
US08871980B2

Reaction notes

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