7-nitro-2-benzyloxy-2,3-dihydro-1H-isoindol-1-one → 7-Amino-2,3-dihydro-2-hydroxy-1H-isoindol-1-one

HRID 511417Notes

Reaction equation

HRID 511417 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[C:11](=[O:13])[N:10]([O:14]CC1C=CC=CC=1)[CH2:9]2)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[C:11](=[O:13])[N:10]([OH:14])[CH2:9]2

Participants

5

Reactant 2

HCID 672541427-nitro-2-benzyloxy-2,3-dihydro-1H-isoindol-1-one2×HCID 178418361HCID 178418361, compound

Product 1

HCID 672547907-Amino-2,3-dihydro-2-hydroxy-1H-isoindol-1-oneYield 609.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-nitro-2-benzyloxy-2,3-dihydro-1H-isoindol-1-one (Compound 186B, 2.3 g, 1.2 mmol) in methanol (30 mL) in a Parr hydrogenation flask was added 200 mg of 5% Pd/C. The mixture was hydrogenated under 40 psi hydrogen pressure at room temperature overnight. The reaction mixture was filtered through a glass filter paper and the filtrate was concentrated to afford 1.2 g of the pure product (90%). 1H NMR (CDCl3, 600 MHz): δ=4.57 (s, 2 H), 5.04 (br, 2 H), 6.57 (d, J=7.8 Hz, 1 H) 6.65 (d, J=7.5 Hz, 1 H), 7.25 (dd, J=7.5, 7.8 Hz, 1 H), 10.2 (s, br, 1 H).

Workup

  1. filtrationThe reaction mixture was filtered through a glass
  2. filtrationfilter paper
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1aaeeb59d9e04352a9fcceea09a8276b
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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