Hydrochloric Acid → 7-Hydroxynaphthalene-2-carbonitrile

HRID 412589Notes

Reaction equation

HRID 412589 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]#[N:14])=[CH:10]2)=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(OCC)(=O)C.Cl>ClC1C=CC=CC=1>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]#[N:14])=[CH:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 109541837-Methoxy-2-naphthonitrile

Product 1

HCID 222436217-Hydroxynaphthalene-2-carbonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a solution of 7-methoxynaphthalene-2-carbonitrile (6 g) in chlorobenzene (60 ml) was added aluminum chloride (15.3 g) at room temperature and the mixture was heated under refluxing for 30 min. After completion of the reaction, the reaction mixture was ice-cooled and ice, ethyl acetate and conc. hydrochloric acid were added, and the mixture was stirred. The organic layer was separated and concentrated. To the obtained residue was added hexane and the resultant solid was collected by filtration and dried under reduced pressure to give the title compound (5.21 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing for 30 min
  3. customAfter completion of the reaction
  4. temperaturecooled
  5. customThe organic layer was separated
  6. concentrationconcentrated
  7. additionTo the obtained residue was added hexane
  8. filtrationthe resultant solid was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-6d71c87dd22c4024a6caaed28affd165
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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