1(3H)-Isobenzofuranone, 3-methyl-6-nitro- → 1(3H)-Isobenzofuranone, 6-amino-3-methyl-

HRID 1061447Notes

Reaction equation

HRID 1061447 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1>C(O)C.[C].[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]([CH3:1])[O:3][C:4]2=[O:5])=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 4877801(3H)-Isobenzofuranone, 3-methyl-6-nitro-

Product 1

HCID 4877771(3H)-Isobenzofuranone, 6-amino-3-methyl-Yield 88.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

78.00 g of 3-methyl-6-nitrophthalide (3-3) was dissolved in 1.2 l of ethanol and 4.0 g of 5% palladium carbon was added thereto, and under a hydrogen atmosphere, the resulting mixture was stirred at a room temperature for 5 hours. The catalyst was filtered off, and thereafter, the filtrate was concentrated under reduced pressure, and the precipitated crystal was purified by recrystallizing (ethanol:water) to obtain 58.21 g of 6-amino-3-methylphtalide (3-4).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe precipitated crystal was purified
  4. customby recrystallizing (ethanol:water)

Sources & evidence

ORD record
ord-88469e83d4ba43ef890dc7e37dd43b85
Source dataset
uspto-grants-2003_02
Patent number
US06525066B2

Reaction notes

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