HCID 54707317, compound → 3-(3-Aminophenyl)-1,5-dihydro-4-hydroxy-2H-pyrrol-2-one

HRID 1655004Notes

Reaction equation

HRID 1655004 reaction equation
[OH:1][C:2]1[CH2:6][NH:5][C:4](=[O:7])[C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1>CO.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([C:3]2[C:4](=[O:7])[NH:5][CH2:6][C:2]=2[OH:1])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 54707317HCID 54707317, compound

Product 1

HCID 547073163-(3-Aminophenyl)-1,5-dihydro-4-hydroxy-2H-pyrrol-2-oneYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1,5-dihydro-4-hydroxy-3-(3-nitrophenyl )-2H-pyrrol-2-one (0.6 g, 2.7 mmol) in methanol (30 ml) was hydrogenated at 30 psi using a palladium on carbon catalyst (200 mg, 35% (w /w)), for 10 min. The catalyst was filtered off and the solvent evaporated in vacuo. The residue was azeotroped with toluene (2×20 ml) and then triturated with ether (20 ml). 3-(3-Aminophenyl)-1,5-dihydro-4-hydroxy-2H-pyrrol-2-one (0.43 g, 84%) was isolated as a pale yellow solid. mp 262°-265° C. (dec.). 1H NMR (360MHz, D6 -DMSO) δ3.80 (2H, s), 6.37 (1H, d, J=8Hz), 6.93 (1H, dd, J=8 and 8Hz), 7.12 (1H, d, J =7Hz), 7.22 (1H, s), 7.45 (1H, s).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated in vacuo
  3. customThe residue was azeotroped with toluene (2×20 ml)
  4. customtriturated with ether (20 ml)

Sources & evidence

ORD record
ord-16c776fbf9f94a8b97e16036bfa1af78
Source dataset
uspto-grants-1995_04
Patent number
US05410049

Reaction notes

Loading…