[1,1'-Biphenyl]-4-amine, 3-nitro- → (1,1'-Biphenyl)-3,4-diamine

HRID 1479118Notes

Reaction equation

HRID 1479118 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.[BH4-].[Na+]>CO.[Pd]>[C:11]1([C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([NH2:1])[CH:10]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 77705[1,1'-Biphenyl]-4-amine, 3-nitro-HCID 4311764Sodium borohydride2×

Product 1

HCID 6452000(1,1'-Biphenyl)-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 2 g (9.3 mmol) of the product obtained in Example 22 in 20 ml of methanol were slowly added 0.2 g of palladium on carbon and 0.7 g of NaBH4. After the addition of NaBH4 had ended, the reaction was already complete. The reaction mixture was filtered through shell lime and washed with ethyl acetate, and the solvent was removed under reduced pressure. This gave 1.3 g (77%).

Workup

  1. filtrationThe reaction mixture was filtered through shell lime
  2. washwashed with ethyl acetate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-07581648165b45efabb16bbce055c610
Source dataset
uspto-grants-2016_08
Patent number
US09406848B2

Reaction notes

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