4-Chloro-4'-nitrobenzophenone → 4-Amino-4'-chlorobenzophenone

HRID 36719Notes

Reaction equation

HRID 36719 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1>C(O)C.[Pt]=O>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 3477714-Chloro-4'-nitrobenzophenone

Product 1

HCID 35287064-Amino-4'-chlorobenzophenoneYield 79.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A suspension of 14.4g (54.8 mmol) of 4-chloro-4'-nitrobenzophenone and 66.9 mg, (0.5 mole %) of platinum oxide was stirred under hydrogen in 300 ml of ethanol for 2 hours The mixture was filtered, evaporated and purified by flash column chromatography (2-8% EtOAc/CH2C12) to obtain 10.05 g (72%) of the desired product as a yellow solid. 1H nmr (CDCl3) δ4.16 (2H, br s), 6.67 (2H, d), 7.43 (2H, d), 7.68 (2H, d), 7.69 (2H, d).

Workup

  1. filtrationwas filtered
  2. customevaporated
  3. custompurified by flash column chromatography (2-8% EtOAc/CH2C12)

Sources & evidence

ORD record
ord-53781cf8028d4ddc9316d7676db2b9e0
Source dataset
uspto-grants-1995_05
Patent number
US05416112

Reaction notes

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