Hydrochloric Acid → 4-Hydroxyisophthalonitrile

HRID 2078417Notes

Reaction equation

HRID 2078417 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[C:11]#[N:12].[Si](I)(C)(C)C.Cl>N1C2C(=CC=CC=2)C=CC=1>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[C:11]#[N:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 50619954-Methoxybenzene-1,3-dicarbonitrile

Product 1

HCID 123259634-HydroxyisophthalonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Conditions

Temperature
120 °C

Procedure

4-Methoxyisophthalonitrile (2 g, 0.12 mol; see step (ii) above) was dissolved in quinoline (20 mL) and TMSI (2.7 mL, 0.018 mol) was added. The reaction mixture was stirred at 120° C. for 14 h, before being cooled to RT, acidified with conc. HCl and extracted with ethyl acetate. The organic layer was washed with 10% aqueous NaOH and the aqueous layer was acidified with 1 N HCl. The product was extracted with ethyl acetate, washed with water and brine and dried over Na2SO4. Solvent evaporation under reduced pressure afforded the sub-title compound (1.1 g, 61%) as pale brown solid. This was employed directly in the next step without further purification.

Workup

  1. temperaturebefore being cooled to RT
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 10% aqueous NaOH
  4. extractionThe product was extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-e840436863ab4267af99fd746a269c03
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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