Pyridine → HCID 68645933, compound

HRID 1160447Notes

Reaction equation

HRID 1160447 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7]C)=[O:6].N1C=CC=C[CH:16]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)(Cl)Cl>[CH3:16][C:3]1[C:2]([NH:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:11][C:10]([N+:12]([O-:14])=[O:13])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 2756518Methyl 3-amino-5-nitrobenzoate

Product 1

HCID 68645933HCID 68645933, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 3-amino-5-nitrobenzoate 24.7 g (126 mmol), pyridine 51 mL (630 mmol), methanesulfonyl chloride 12 mL (151 mmol) and chloroform (250 mL) was stirred at 40° C. for 5 hours. The solvent was evaporated and to the residue was added 1N hydrochloric acid and the mixture was extracted with ethyl acetate 500 mL. The organic layer was washed with 1N hydrochloric acid and 5% aqueous sodium chloride solution and dried on magnesium sulfate. The solvent was evaporated and the residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane to give 32.1 g (117 mmol) of the title compound (yield: 93%).

Workup

  1. customThe solvent was evaporated and to the residue
  2. additionwas added 1N hydrochloric acid
  3. extractionthe mixture was extracted with ethyl acetate 500 mL
  4. washThe organic layer was washed with 1N hydrochloric acid and 5% aqueous sodium chloride solution
  5. customdried on magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-753a9800d95d428f98ee02897e8cf66f
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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