Water → 2-Hydroxy-4-nitrobenzonitrile

HRID 18458

Reaction equation

HRID 18458 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13].O>CCOC(C)=O>[OH:9][C:10]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 2918672-Methoxy-4-nitrobenzonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 2861482-Hydroxy-4-nitrobenzonitrileYield 95.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Pyridine hydrochloride (100 g; 0.87 mol) and 2-methoxy-4-nitro-benzonitrile (17 g; ca 96 mmol) was heated to 200° C. for 2 hours, cooled to room temperature and carefully added H2O and EtOAc. The slurry was stirred until all solid dissolved. The organic layer was isolated, washed twice with H2O, brine then dried, filtered and evaporated to dryness to yield 15 g (95%) pure product

Workup

  1. dissolutiondissolved
  2. customThe organic layer was isolated
  3. washwashed twice with H2O, brine
  4. customthen dried
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-572a2f4a537f4d7ba786d836abdcf52a
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Linked notes

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