Hydrochloric Acid → 4-Hydroxy-3-isopropenyl-5-nitrobenzonitrile

HRID 2093614Notes

Reaction equation

HRID 2093614 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12]C)[C:7]#[N:8])([CH3:3])=[CH2:2].Cl.N1C=CC=CC=1.Cl>>[OH:12][C:11]1[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[C:1]([CH3:3])=[CH2:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 671408193-Isopropenyl-4-methoxy-5-nitrobenzonitrile

Product 1

HCID 671407854-Hydroxy-3-isopropenyl-5-nitrobenzonitrile

Procedure

A mixture of 3-isopropenyl-4-methoxy-5-nitrobenzonitrile (5.06 g, 23.19 mmol) and pyridine hydrochloride (10 g, 87 mmol) was placed in an oil bath at 200° C. for 4 min. The reaction mixture was then cooled to room temperature, added 1M HCl, and extracted 3 times with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography using a Horizon Biotage, 65i Si column, eluting with 1 column volume of 1% ethyl acetate in hexanes, followed by a linear gradient of ethyl acetate in hexanes from 1% to 100% over 10 column volumes to afford the title compound. Mass spectrum (ESI) 203.1 (M−1).

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography
  7. washeluting with 1 column volume of 1% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-db768f989bd34667b3cf784d91f9bf0b
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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