4-Aminophenol → HCID 14499215, compound

HRID 1194506Notes

Reaction equation

HRID 1194506 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](O)[CH:6]=[CH:5]2.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.S(=O)(O)[O-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 271446-Bromo-2-naphthalenolHCID 23665763Sodium Bisulfite

Product 1

HCID 14499215HCID 14499215, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 334 mg (1.50 mmol, Aldrich) of 6-bromo-2-naphthol, 218 mg (2.00 mmol, Aldrich) of 4-aminophenol, and 1.0 g of sodium bisulfite in 5 ml of H2O was heated to 150° in a closed Pyrex tube for 76 hours. The reaction was cooled, added to 25 ml of H2O and extracted with 25 ml of ethyl acetate. The organic extract was dried (MgSO4) and concentrated in vacuo to give a solid. The crude solid was purified by flash chromatography (10×5.0 cm, 1:4 EtOAc/petroleum ether) followed by recrystallization (EtOAc/petroleum ether) to afford 330 mg (70%) of title compound as small grey-white crystals, m.p. 179°-180°.

Workup

  1. temperaturewas heated to 150° in a closed Pyrex tube for 76 hours
  2. temperatureThe reaction was cooled
  3. extractionextracted with 25 ml of ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a solid
  8. customThe crude solid was purified by flash chromatography (10×5.0 cm, 1:4 EtOAc/petroleum ether)
  9. customfollowed by recrystallization (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-c4c9d58335b94b37adc464d43b13cf69
Source dataset
uspto-grants-1989_03
Patent number
US04814454

Reaction notes

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