4-Aminophenol → 6-[(4-Hydroxyphenyl)amino]-2-naphthalenol

HRID 1194499

Reaction equation

HRID 1194499 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15](O)[CH:16]=2)[CH:11]=1.S(=O)(O)[O-].[Na+]>O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([OH:9])[CH:19]=[CH:18]3)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 935522,6-DihydroxynaphthaleneHCID 23665763Sodium Bisulfite

Product 1

HCID 144992086-[(4-Hydroxyphenyl)amino]-2-naphthalenolYield 31.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 300 mg (2.75 mmol, Aldrich) of 4-aminophenol, 1.5 g (90%, 8.4 mmol, Aldrich) of 2,6-dihydroxynaphthalene and 1.0 g (9.6 mmol, Aldrich), of sodium bisulfite in 30 ml of H2O was refluxed for 18 hours. The reaction mixture was cooled, added to 30 ml of H2O and extracted with two 25 ml portions of ethyl acetate. The organic extracts were combined, dried (MgSO4), and concentrated in vacuo to give a solid. The crude solid was purified by flash chromatography (15×5.0 cm, 1:2 EtOAc/pet ether) followed by recrystallization (EtOAc/pet ether) to afford 215 mg (31%) of title compound as pale pink crystals, m.p. 195°-196°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with two 25 ml portions of ethyl acetate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customThe crude solid was purified by flash chromatography (15×5.0 cm, 1:2 EtOAc/pet ether)
  7. customfollowed by recrystallization (EtOAc/pet ether)

Sources & evidence

ORD record
ord-923e4304ef314a089afc1df6a7a23b49
Source dataset
uspto-grants-1989_03
Patent number
US04814454

Linked notes

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