6-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman → 6-Amino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

HRID 2179894Notes

Reaction equation

HRID 2179894 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[O:10][CH:9]([CH3:26])[CH2:8]2)(=O)C>OS(O)(=O)=O.CO>[NH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]([C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[O:10][CH:9]([CH3:26])[CH2:8]2

Participants

4

Reactant 1

HCID 224889656-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Product 1

HCID 224889636-Amino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochromanYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

Solution of 14 (0.114 g, 0.32 mmol) in 5 ml of 4N H2SO4 and 5 ml of methanol was heated to reflux. After refluxing for 15 hours, the methanol was removed under reduced pressure. The remaining aqueous solution was neutralized with NaHCO3 to pH 9, followed by extraction with ethyl acetate three times. The combined organic phase was dried over Na2SO4. Removal of the solvent afforded the desired product 15 (100 mg, 100%) which was used directly for next step.

Workup

  1. temperatureAfter refluxing for 15 hours
  2. customthe methanol was removed under reduced pressure
  3. extractionfollowed by extraction with ethyl acetate three times
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-bcaf7ce804d44b1197cc1f58fe517e70
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

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