Sodium borohydride → (1,1'-Biphenyl)-3,4-diamine

HRID 1479120Notes

Reaction equation

HRID 1479120 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=CC=CC=3)[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:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 106830162-Nitro-4-(2-naphthyl)aniline

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 product obtained in Example 28 in 20 ml of methanol are slowly added 0.2 g of palladium on carbon and 0.7 g of NaBH4. After the addition of NaBH4 has ended, the reaction is already complete. The reaction mixture is filtered through shell lime and washed with ethyl acetate, and the solvents are removed under reduced pressure. This gives 1.52 g (70%).

Workup

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

Sources & evidence

ORD record
ord-86021d38cc494f6eaef7b6430229a86d
Source dataset
uspto-grants-2016_08
Patent number
US09406848B2

Reaction notes

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