(4-Amino-3-nitrophenyl)methanol → (3,4-Diaminophenyl)methanol

HRID 26381Notes

Reaction equation

HRID 26381 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-])=O.[H][H]>[Ni].O1CCCC1>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[NH2:1])[CH2:6][OH:7]

Participants

5

Reactant 2

HCID 12902831(4-Amino-3-nitrophenyl)methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 12902832(3,4-Diaminophenyl)methanolYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Six grams (0.035 mole) of 4-amino-3-nitrobenzyl alcohol, 95 ml. of tetrahydrofuran and 0.5 g. of Raney Nickel were hydrogenated at 40 psi at room temperature until 3 moles of hydrogen were absorbed. The catalyst was filtered and the filtrate was evaporated in vacuo to yield 4.83 g. (82 percent yield) of 3,4-diaminobenzyl alcohol, mp 74°-75° C.

Workup

  1. customwere absorbed
  2. filtrationThe catalyst was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customto yield 4.83 g

Sources & evidence

ORD record
ord-a129f758d77a474399978123313f4150
Source dataset
uspto-grants-1979_04
Patent number
US04150028

Reaction notes

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