p-Toluenesulfonic acid → 6-Amino-1,3-dihydro-2H-indol-2-one

HRID 857434Notes

Reaction equation

HRID 857434 reaction equation
C1[N:5]([CH2:6][O:7]CCO)[C:4]2NC(N)=[N:13][C:14](=O)[C:3]=2N=1.[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=[CH:19][CH:18]=1>C(O)C>[NH2:13][C:14]1[CH:3]=[C:4]2[C:18]([CH2:19][C:6](=[O:7])[NH:5]2)=[CH:17][CH:22]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178508935HCID 178508935, compound

Product 1

HCID 5905386-Amino-1,3-dihydro-2H-indol-2-oneYield 3,626.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-dinitrophenylacetic acic (10 g; 44 mmol) was dissolved in ethanol (200 mL) and purged with N2. 10% Pd/C (400 mg) was added and the reaction hydrogenated at 45 psi for 2 hours. The reacton was then transferred to a RBF and p-toluenesulfonic acid (150 mg) was added and the reaction heated at reflux overnight. The reaction was then filtered through celite to remove catalyst and concentrated. The product crashed out and was filtered as tan crystals 4.68 g (72% yield). 1H NMR (DMSO-d6, 400 MHz) δ 3.20 (s, 2H), 4.97 (br s, 2H), 6.07 (m, 2H), 6.76 (d, J=8.7 Hz; 1H), 10.05 (s, 1H); HPLC ret. time: 2.123 min. LRMS (M+) 148.7.

Workup

  1. custompurged with N2
  2. addition10% Pd/C (400 mg) was added
  3. customthe reaction hydrogenated at 45 psi for 2 hours
  4. additionwas added
  5. temperaturethe reaction heated
  6. temperatureat reflux overnight
  7. filtrationThe reaction was then filtered through celite
  8. customto remove catalyst
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a16fe0d064d14fdfa1c7c57ec5ec3b83
Source dataset
uspto-grants-2006_12
Patent number
US07145008B2

Reaction notes

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