4-Amino-3-nitrobenzophenone → 3,4-Diaminobenzophenone

HRID 46703

Reaction equation

HRID 46703 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[N+:16]([O-])=O.[H][H]>[Ni].O1CCCC1>[NH2:16][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:2]=1[NH2:1])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 5969704-Amino-3-nitrobenzophenoneHCID 178418361HCID 178418361, compound

Product 1

HCID 1355203,4-DiaminobenzophenoneYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Fifty grams of 4-amino-3-nitrobenzophenone were hydrogenated at room temperature in 945 ml. of tetrahydrofuran with 15 g. of Raney nickel at 2.74×106 dynes/cm.2. After 4 hours three equivalents of hydrogen were absorbed. The catalyst was filtered and the filtrate was evaporated in vacuo to a solid residue. The residue was chromatographed over silica gel using ethyl acetate as eluant. Fractions 5-9 were combined to yield 43.6 g. (100 percent yield) of 3,4-diaminobenzophenone.

Workup

  1. customwere hydrogenated at room temperature in 945 ml
  2. filtrationThe catalyst was filtered
  3. customthe filtrate was evaporated in vacuo to a solid residue
  4. customThe residue was chromatographed over silica gel
  5. customto yield 43.6 g

Sources & evidence

ORD record
ord-bd49cab44b95447da5649a4e21c24752
Source dataset
uspto-grants-1979_11
Patent number
US04174454

Linked notes

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