HCID 67253776, compound → 7-Amino-2,3,3-trimethyl-2,3-dihydro-1H-isoindol-1-one

HRID 1947933Notes

Reaction equation

HRID 1947933 reaction equation
[CH3:1][N:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[C:5]([N+:13]([O-])=O)[CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:16]>C(O)C.[Pd]>[NH2:13][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3](=[O:16])[N:2]([CH3:1])[C:10]2([CH3:12])[CH3:11]

Participants

4

Reactant 1

HCID 67253776HCID 67253776, compound2×

Product 1

HCID 672553277-Amino-2,3,3-trimethyl-2,3-dihydro-1H-isoindol-1-oneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

20 mg of 5% Pd/C was cautiously added to a solution of 2,3,3-trimethyl-7-nitroisoindolin-1-one (Compound 148B, 0.15 g, 0.68 mmol) in ethanol (5 mL), and stirred under hydrogen atmosphere at room temperature overnight. The reaction mixture was and concentrated to remove ethanol to provide 80 mg of pure the title compound (62%). 1H NMR (CDCl3, 500 MHz): δ1.36 (s, 6H), 3.58 (s, 3H), 3.60 (brs, 2H), 6.58 (d, J=8.0 Hz, 1H), 6.69 (d, J=7.0 Hz, 1H), 6.84 (dd, J=7.0, 8.0 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. customto remove ethanol

Sources & evidence

ORD record
ord-d8dccb8132ee4f2ea10166b4b8ab1585
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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