7-Hydroxy-2-methyl-6-nitro-2,3-dihydroisoindol-1-one → 6-Amino-7-hydroxy-2-methyl-2,3-dihydroisoindol-1-one

HRID 1528170Notes

Reaction equation

HRID 1528170 reaction equation
[OH:1][C:2]1[C:3]([N+:13]([O-])=O)=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2>[Pd].CO>[NH2:13][C:3]1[C:2]([OH:1])=[C:10]2[C:6]([CH2:7][N:8]([CH3:12])[C:9]2=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 895250337-Hydroxy-2-methyl-6-nitro-2,3-dihydroisoindol-1-one

Product 1

HCID 895253686-Amino-7-hydroxy-2-methyl-2,3-dihydroisoindol-1-oneYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

38 mg of palladium on carbon at 10% were added to a solution of 0.35 g (1.68 mmol) of 7-hydroxy-2-methyl-6-nitro-2,3-dihydroisoindol-1-one in 20 ml of methanol under nitrogen. The reaction medium was stirred under a hydrogen atmosphere for 18 hours. The reaction medium was filtered and concentrated. The residue was chromatographed on a prepacked C18 column (12 g column, 30 ml/min, 95/5 water/acetonitrile). 0.19 g of product was obtained in the form of a brown oil. Yield=64%.

Workup

  1. filtrationThe reaction medium was filtered
  2. concentrationconcentrated
  3. customThe residue was chromatographed on a prepacked C18 column (12 g column, 30 ml/min, 95/5 water/acetonitrile)

Sources & evidence

ORD record
ord-0d143d7b2f054ef5967c26459da127c6
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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