Sulfuric Acid → 2-Hydroxyimino-2-(1-naphthyl)acetonitrile

HRID 597689

Reaction equation

HRID 597689 reaction equation
[C:1]1([CH2:11][C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].S(=O)(=O)(O)O.[N:21]([O-:23])=[O:22].[Na+]>CO.O>[N:21]([O:23][CH3:1])=[O:22].[OH:22][N:21]=[C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:12]#[N:13]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 85961-NaphthaleneacetonitrileHCID 14798Sodium HydroxideHCID 23668193Sodium Nitrite

Product 2

HCID 12231Methyl nitriteHCID 736804482-Hydroxyimino-2-(1-naphthyl)acetonitrileYield 72.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

2-(1-naphthyl)acetonitrile (16.7 g.) was added to a solution of sodium hydroxide (4.2 g.) in methanol (80 ml.). Gaseous methyl nitrite which was prepared by adding a solution of concentrated sulfuric acid (5 ml.) in water (10 ml.) to a solution of sodium nitrite (8.3 g.) in a mixture of methanol was introduced, under ice-cooling, and water (5 ml.). The mixture was stirred for 4 hours at the same temperature and the reaction mixture was treated by a conventional method to give 2-hydroxyimino-2-(1-naphthyl)acetonitrile (7.1 g.), oil.

Workup

  1. additionwas introduced, under ice-
  2. temperaturecooling
  3. additionthe reaction mixture was treated by a conventional method

Sources & evidence

ORD record
ord-8f1c3c64db864963ae99b61fcf7561f3
Source dataset
uspto-grants-1977_03
Patent number
US04014915

Linked notes

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