6-Bromo-2-naphthalenol → 6-Hydroxy-2-naphthonitrile

HRID 1534772Notes

Reaction equation

HRID 1534772 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([OH:15])[CH:9]=[CH:8]2>CN1CCCC1=O.O.Cl.[Fe](Cl)(Cl)Cl>[C:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([OH:15])[CH:9]=[CH:8]2)#[N:3]

Participants

7

Reactant 2

HCID 271446-Bromo-2-naphthalenolHCID 178418546HCID 178418546, compound

Product 1

HCID 45894766-Hydroxy-2-naphthonitrileYield 54.8%

Reagents, catalysts & solvents 4

HCID 24380Iron chloride (FeCl3)CatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

Copper (I) cyanide (2.73 g, 0.03 mol) was added to a solution containing 5 g (0.022 mol) 6-bromo-2-hydroxynaphthalene in 25 ml of dry N-methyl-2-pyrrolidinone and refluxed at 200° C. under nitrogen for 1.5 h. The reaction mixture was cooled to 100° C., poured into a solution of iron(III) chloride (5.9 g) in water (91 ml) and concentrated hydrochloric acid (3.18 ml), and stirred at 60° C. for 30 min. The obtained mixture was extracted with ethyl ether. The ether layer was treated with charcoal, dried over anhydrous sodium sulfate, and then evaporated to dryness. The obtained solid was recrystallized from water to yield 2.04 g (54%) white solid. 1H-NMR (CDCl3, TMS, δ in ppm): 5.60 (s, 1H, --OH), 7.10-8.07 (m, 6, aromatic protons).

Workup

  1. temperatureThe reaction mixture was cooled to 100° C.
  2. extractionThe obtained mixture was extracted with ethyl ether
  3. additionThe ether layer was treated with charcoal
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe obtained solid was recrystallized from water

Sources & evidence

ORD record
ord-082667b0685c496081745f64f7eeda0e
Source dataset
uspto-grants-1992_02
Patent number
US05091274

Reaction notes

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