2-Methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one → 7-Amino-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 511233Notes

Reaction equation

HRID 511233 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[C:5]([N+:11]([O-])=O)[CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:14]>C(Cl)Cl.C(O)C.[Pd]>[NH2:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3](=[O:14])[N:2]([CH3:1])[CH2:10]2

Participants

4

Reactant 1

HCID 587485312-Methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 450887127-Amino-2-methyl-2,3-dihydro-1H-isoindol-1-oneYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

A solution of 2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (6.09 g, 31 mmol) in DCM:ethanol (8:2) was hydrogenated under 40 psi of H2 in the presence of 5% Pd/C (500 mg) until cessation of H2 uptake. The reaction mixture was filtered, and the filtrate dried (Na2SO4) and concentrated in vacuo to afford 4.45 g of 7-amino-2-methyl-2,3-dihydro-1H-isoindol-1-one (XXXVIII, yield: 73%). 1H NMR (CDCl3, 400 MHz): δ 3.11 (s, 3H), 4.27 (s, 2H), 5.19 (bs, 2H), 5.5 (d, 1H, J=7.8 Hz), 6.71 (d, 1H, J=7.2 Hz).

Workup

  1. filtrationThe reaction mixture was filtered
  2. dry with materialthe filtrate dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79280f91e5c5431c9686e0e4f8b2fd92
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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