Sulfuric Acid → HCID 21714399, compound

HRID 650107Notes

Reaction equation

HRID 650107 reaction equation
[C:1]([C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:10])#[N:2].[N+:11]([O-])([O-:13])=[O:12].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:11]([C:5]1[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([C:1]#[N:2])[C:4]=1[OH:10])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 44079952-Chloro-6-hydroxybenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 21714399HCID 21714399, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-cyano-3-chlorophenol(2.8 g, 18.3 mmol) was dissolved in methylene chloride(40 ml) followed by the addition of sodium nitrate (1.70 g, 20.1 mmol). The addition of sulfuric acid (15 ml/ 3M) is then made, followed by addition of a catalytic amount of sodium nitrite. The mixture is allowed to stir. After 24 hrs, the reaction mixture is diluted with methylene chloride and extracted with water. The organic layer is 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(1.05 g, 29.2%). 1H NMR (CD3COCD3): δ8.09 (d,1H), 6.55 (d, 1H).

Workup

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

Sources & evidence

ORD record
ord-b4e57e296ab54723b9453373aa2395f6
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Reaction notes

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