Sulfuric Acid → 8-Azidonaphthalen-1-ol

HRID 1580533Notes

Reaction equation

HRID 1580533 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12](N)=[CH:11][CH:10]=[CH:9]2)=[N+:2]=[N-:3].S(=O)(=O)(O)[OH:16].N([O-])=O.[Na+]>O>[N:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[OH:16])[CH:7]=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 120253881-Naphthalenamine, 8-azido-HCID 23668193Sodium Nitrite

Product 1

HCID 215619898-Azidonaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of 8-azido-1-naphthylamine (0.368 g., 0.02 mole) was dissolved in warm, dilute sulfuric acid (3 ml. of conc. H2SO4 diluted with 30 ml. of water). The solution was cooled to O°C. and diazotized with a solution of NaNO2 (160 mg., 0.023 mole) in 2 ml. of water. The excess of nitrous acid was destroyed by the addition of urea. The yellow solution of the diazonium salt was diluted with 100 ml. of water and heated at 60°for 1.5 hr. The precipitated material was washed with water, dried and filtered through activated charcoal. Removal of ether left a residue which weighed 35 mg. Recrystallization from petroleum ether gave 1-azido-8-hydroxynaphthalene in the form of pale yellow needles (20 mg., 5.4 percent), m.p. 65°C.-67°C.

Workup

  1. temperaturein warm
  2. temperatureThe solution was cooled to O°C
  3. customThe excess of nitrous acid was destroyed by the addition of urea
  4. additionThe yellow solution of the diazonium salt was diluted with 100 ml
  5. temperatureof water and heated at 60°for 1.5 hr
  6. washThe precipitated material was washed with water
  7. customdried
  8. filtrationfiltered through activated charcoal
  9. customRemoval of ether
  10. waitleft a residue which
  11. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-8665a939ec6448d6ad4df13c68c0dfdf
Source dataset
uspto-grants-1976_01
Patent number
US03933497

Reaction notes

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