Hydrochloric Acid → 7-Hydroxy-3-(3-hydroxyphenyl)-1-naphthonitrile

HRID 1035671Notes

Reaction equation

HRID 1035671 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=3)[CH:9]=[C:10]2[C:13]#[N:14])=[CH:5][CH:4]=1.Cl.[NH+]1C=CC=CC=1.Cl>>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=3)[CH:9]=[C:10]2[C:13]#[N:14])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21584435Pyridinium hydrochlorideHCID 594434777-Methoxy-3-(3-methoxyphenyl)-1-naphthonitrile

Product 1

HCID 249505517-Hydroxy-3-(3-hydroxyphenyl)-1-naphthonitrileYield 62%

Procedure

7-Methoxy-3-(3-methoxyphenyl)-1-naphthonitrile (110 mg, 0.39 mmol, 1 eq) and pyridinium hydrochloride (4.76 mmol, 12.2 eq) are boiled under reflux for 3 h. After cooling the reaction mixture, it is acidified with 1 N HCl, the resulting precipitate is filtered and dissolved in a small amount of ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. The residue formed is the desired product (yield 62%, 63 mg).

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling the reaction mixture, it
  3. filtrationthe resulting precipitate is filtered
  4. dissolutiondissolved in a small amount of ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum on a rotary evaporator
  9. customThe residue formed

Sources & evidence

ORD record
ord-4551d881bffd480aace8e67739ed6961
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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