2-Methyl-4-methoxy-5-nitrophenyl mesylate → 2-Methyl-4-methoxy-5-aminophenyl mesylate

HRID 1029998Notes

Reaction equation

HRID 1029998 reaction equation
[S:1]([O:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]([O:15][CH3:16])=[CH:8][C:7]=1[CH3:17])(=[O:4])(=[O:3])[CH3:2]>[Pd].C(O)C>[S:1]([O:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([O:15][CH3:16])=[CH:8][C:7]=1[CH3:17])(=[O:4])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 198211562-Methyl-4-methoxy-5-nitrophenyl mesylate

Product 1

HCID 198211482-Methyl-4-methoxy-5-aminophenyl mesylateYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.55 g of 10% palladium-on-carbon, 18.8 g (71.9 mmol) of 2-methyl-4-methoxy-5-nitrophenyl mesylate and 120 ml of ethanol were fed into an autoclave (200 ml), and the mixture was then hydrogenated at 50° C. under 50 g/cm2 for 1 hours with stirring. After allowing to cool, palladium-on-carbon was filtered off and the solvent was distilled off under reduced pressure to obtain brown crystals. The crystals thus obtained were recrystallized from ethanol to thereby give 13.4 g (58.2 mmol) of 2-methyl-4-methoxy-5-aminophenyl mesylate in the form of yellow needle-like crystals. The yield was 81%.

Workup

  1. temperatureto cool
  2. filtrationpalladium-on-carbon was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto obtain brown crystals
  5. customThe crystals thus obtained
  6. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-721c1db3f9a14e7883e496ee74a8c4fe
Source dataset
uspto-grants-1992_04
Patent number
US05104414

Reaction notes

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