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

HRID 1629863Notes

Reaction equation

HRID 1629863 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-fac16e57d9a54070b1ca600be030c65e
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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