Sulfuric Acid → 2-Hydroxy-3-nitrobenzonitrile

HRID 568034

Reaction equation

HRID 568034 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].[N+:10]([O-])([O-:12])=[O:11].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[C:4]=1[OH:9])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 119072-HydroxybenzonitrileHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

Product 1

HCID 124686862-Hydroxy-3-nitrobenzonitrileYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-cyanophenol (2.38 g, 20 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.88 g, 22 mmol). The addition of sulfuric acid (20 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(1.4 g, 42%). 1H NMR (CD3COCD3): δ 8.47 (d,1H), 8.15 (d, 1H), 7.30 (t, 1H).

Workup

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-517c485d1d6f47c596a8b2db62e1e607
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Linked notes

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