Hydrochloric Acid → 158580-87-1

HRID 841174Notes

Reaction equation

HRID 841174 reaction equation
Cl.[N+:2]([C:5]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])([O-])=O>CO>[NH2:2][C:5]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22621045HCID 22621045, compound

Product 1

HCID 22620941158580-87-1Yield 203.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (90 ml) was added to a stirred suspension of methyl 2-nitro-4-methylsulphonylbenzoate (25 g) in methanol at −5° C. (ice/salt bath). The cooling bath was then removed and iron dust (175 g) was added portionwise over a period of 20 minutes. The resulting exotherm was controlled using a cooling bath so that the temperature did not exceed 50° C. After 15 minutes of cooling, the bath was removed and the reaction mixture was allowed to reach room temperature. Stirring was continued for a further 3 hours. The mixture was poured onto ice and then neutralised with sodium carbonate. Dichloromethane was added and the suspension was filtered. The filtrate was extracted with further dichloromethane and the combined organic extracts were dried (magnesium sulphate), filtered and evaporated to yield a crude product which was purified by recrystallisation from ethyl acetate/hexane to give methyl 2-amino-4methylsulphonylbenzoate (45 g) as yellow needles, m.p. 98.3-98.5° C.

Workup

  1. customThe cooling bath was then removed
  2. additioniron dust (175 g) was added portionwise over a period of 20 minutes
  3. customdid not exceed 50° C
  4. temperatureAfter 15 minutes of cooling
  5. customthe bath was removed
  6. customto reach room temperature
  7. additionThe mixture was poured onto ice
  8. additionDichloromethane was added
  9. filtrationthe suspension was filtered
  10. extractionThe filtrate was extracted with further dichloromethane
  11. dry with materialthe combined organic extracts were dried (magnesium sulphate)
  12. filtrationfiltered
  13. customevaporated
  14. customto yield a crude product which
  15. customwas purified by recrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4b8bf06f17dc4403abc1a047af8ff3b9
Source dataset
uspto-grants-2002_04
Patent number
US06369270B1

Reaction notes

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