Sulfuric Acid → Methyl 3-chloro-4-nitroso-benzoate

HRID 2094294Notes

Reaction equation

HRID 2094294 reaction equation
[K].S(=O)(=O)(O)O.C(=O)([O-])[O-:8].[Na+].[Na+].[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[Cl:24]>O>[Cl:24][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:14]=1[N:13]=[O:8])[C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 1515284Methyl 4-Amino-3-chlorobenzoateHCID 5462222Potassium

Product 1

HCID 86069447Methyl 3-chloro-4-nitroso-benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.00 g (29.6 mmol) potassium peroxodisulphate are added to 6.0 ml of conc. sulphuric acid with stirring, stirred for 30 minutes at ambient temperature under a nitrogen atmosphere, the mixture is stirred into 50 g ice and neutralised with 14 g sodium carbonate. The solution obtained is combined with a suspension of 2.78 g (15.0 mmol) methyl 4-amino-3-chloro-benzoate in 300 ml of water and stirred for 16 hours at ambient temperature. The reaction mixture is suction filtered, the filter cake is washed with water, dried in the air and purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 9:1).

Workup

  1. stirringstirred for 30 minutes at ambient temperature under a nitrogen atmosphere
  2. customThe solution obtained
  3. stirringstirred for 16 hours at ambient temperature
  4. filtrationfiltered
  5. washthe filter cake is washed with water
  6. customdried in the air
  7. custompurified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-686e905ed2d5471eb8c3f6174a5b0a82
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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