Ethanol → (5-Amino-2-chlorophenyl)(phenyl)methanone

HRID 392440

Reaction equation

HRID 392440 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[Sn](Cl)Cl.C(O)C.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:16][C:13]1[CH:14]=[CH:15][C:2]([Cl:1])=[C:3]([CH:12]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 24479Stannous ChlorideHCID 1185912-Chloro-5-nitrobenzophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 10489713(5-Amino-2-chlorophenyl)(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloro-5-nitrobenzophenone (1.3 g,5.0 mmol), tin(II) chloride (4.5 g, 20 mmol), and ethanol (20 ml) were mixed and heated at 70° C. for 1 h. After cooling to room temperature, to the reaction mixture were added ice, EtOAc and aqueous NaHCO3 and it was stirred for 30 min. The organic layer was washed with brine and dried over MgSO4. Filtration and evaporation afforded 5-amino-2-Chlorobenzophenone. 1H NMR, 7.85(m,2H), 7.30-7.66 (m,3H7.20 (d,1H,J=8.8 Hz), 6.60-6.80 (m,2H). MS calcd 231.1; MS (M+1) 232.0.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-e1b29d11510c40008c7c6efbe6135613
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Linked notes

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