4-Aminophenol → 4-(2-Naphthylamino)phenol

HRID 1165490Notes

Reaction equation

HRID 1165490 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.S(=O)(O)[O-].[Na+]>O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 86632-NaphtholHCID 23665763Sodium Bisulfite

Product 1

HCID 71414-(2-Naphthylamino)phenolYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1.00 g (6.94 mmol, Aldrich) of 2-naphthol, 1.01 g (9.26 mmol, Aldrich) of 4-aminophenol, and 5.2 g (50 mmol, Aldrich) of sodium bisulfite in 30 ml of H2O was refluxed for 36 hours. The reaction mixture was cooled, added to 50 ml of H2O and extracted with 50 ml of hot ethyl acetate. The organic layer was separated, washed with an additional 50 ml of H2O, dried (MgSO4) and concentrated in vacuo to give a solid. The crude solid was purified by flash chromatography (15×5.0 cm, 1:4 EtOAc/petroleum ether) followed by recrystallization (EtOAc/petroleum ether) to afford 1.15 g (71%) of title compound as pale purple flakes, m.p. 134°-135° C.

Workup

  1. temperaturewas refluxed for 36 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with 50 ml of hot ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with an additional 50 ml of H2O
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a solid
  9. customThe crude solid was purified by flash chromatography (15×5.0 cm, 1:4 EtOAc/petroleum ether)
  10. customfollowed by recrystallization (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-51d9b8c02c3d4a3f8b9212d850476383
Source dataset
uspto-grants-1990_03
Patent number
US04910208

Reaction notes

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