HCID 67254135, compound → 7-Amino-2,3-dimethyl-2,3-dihydro-isoindol-1-one

HRID 511380Notes

Reaction equation

HRID 511380 reaction equation
O[C:2]1([CH3:16])[C:10]2[C:5](=[C:6]([N+:11]([O-])=O)[CH:7]=[CH:8][CH:9]=2)[C:4](=[O:14])[N:3]1[CH3:15].[H][H]>[Pd].CC(O)=O>[NH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[C:4](=[O:14])[N:3]([CH3:15])[CH:2]2[CH3:16]

Participants

5

Reactant 2

HCID 67254135HCID 67254135, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 585226217-Amino-2,3-dimethyl-2,3-dihydro-isoindol-1-oneYield 50.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-hydroxy-2,3-dimethyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (Compound 1578, 500 mg), AcOH (12 mL), and 5% Pd/C (60 mg) was hydrogenated for 14 h under 1 atm hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated, residue was purified by column chromatography to afford 200 mg of the title compound (yield: 50%). 1H NMR (CDCl3, 300 MHz): δ=1.43 (d, J=6.8 Hz, 3 H), 3.04 (s, 3 H), 4.33 (q, J=6.3 Hz, 1 H), 5.20 (s, br, 2 H), 6.55 (d, J=8.1 Hz, 1 H), 7.21-7.26 (m, 2 H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customresidue was purified by column chromatography

Sources & evidence

ORD record
ord-7ced293abf29499b98aa39adb98378cc
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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