1(3H)-Isobenzofuranone, 3-methyl-6-nitro- → 1(3H)-Isobenzofuranone, 6-amino-3-methyl-
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe catalyst was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customthe precipitated crystal was purified
- 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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