HCID 67253776, compound → HCID 67255327, compound

HRID 511365Notes

Reaction equation

HRID 511365 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 67255327HCID 67255327, compoundYield 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): δ 1.36 (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-562ab1c0220945949e9e45a1926a3e51
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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