Water → 2-Hydroxy-6-nitrobenzonitrile

HRID 711731Notes

Reaction equation

HRID 711731 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:4]=1[C:5]#[N:6].Cl.N1C=CC=CC=1.O>C(Cl)Cl>[OH:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 380482-Methoxy-6-nitrobenzonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 125032052-Hydroxy-6-nitrobenzonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

2-Methoxy-6-nitrobenzonitrile (Example 129f) (10.73 g, 60.2 mmol) and pyridine hydrochloride (16.0 g, 138 mmol) were mixed together as solids under nitrogen, and then heated in a preheated oil bath at 200° C. for 40 min. After cooling to room temperature, water (200 mL) and CH2Cl2 (200 mL) were added and stirred vigorously for 1 hour. Then, the precipitated product was collected by filtration and recrystallized from water, to give 8.2 g, (83%) of 2-hydroxy-6-nitrobenzonitrile as a brown solid. 1H-NMR (400 MHz, DMSO-d6) δ 12.13 (broad s, 1H), 7.68-7.79 (m, 2H), 7.39-7.44 (m, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThen, the precipitated product was collected by filtration
  3. customrecrystallized from water

Sources & evidence

ORD record
ord-4e7d7b6dbc1e4cf7b848b83bc6219ff8
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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