Acetic Acid → 6-Amino-1,3-dihydro-2H-indol-2-one

HRID 1615199Notes

Reaction equation

HRID 1615199 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=O)([O-])=O.CC(O)=O>[Pd].CO>[NH2:10][C:8]1[CH:9]=[C:4]2[C:5]([CH2:13][C:14](=[O:16])[NH:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 2215132,4-Dinitrophenylacetic acid

Product 1

HCID 5905386-Amino-1,3-dihydro-2H-indol-2-oneYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(2,4-dinitrophenyl)acetic acid (1.0 g, 4.42 mmol), AcOH (10 mL), and MeOH (5 mL) was purged with Ar for 15 minutes at which time 10 wt. % Pd/C (100 mg) was added. The mixture was then purged briefly with H2 and then stirred under 1 atm of H2 overnight. The mixture was filtered through a pad of celite, the solvent removed in vacuo, and the residue purified by column chromatography (silica gel, 90:10 CH2Cl2/MeOH) to give 462 mg, 71% of a brown solid. 1H NMR (400 MHz, CD3OD) δ 6.95 (d, J=7.7 Hz, 1H), 6.37 (d, J=7.8 Hz, 1H), 6.34 (s, 1H), 3.38 (s, 2H); MS ESI 149.0 [M+H]+, calcd for [C8H8N2O+H]+149.07.

Workup

  1. additionwas added
  2. customThe mixture was then purged briefly with H2
  3. filtrationThe mixture was filtered through a pad of celite
  4. customthe solvent removed in vacuo
  5. customthe residue purified by column chromatography (silica gel, 90:10 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-875aa3e9bc5640319a6637237c365865
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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