HCID 54707314, compound → HCID 54707315, compound

HRID 1655006Notes

Reaction equation

HRID 1655006 reaction equation
[OH:1][C:2]1[CH2:6][N:5]([CH3:7])[C:4](=[O:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1>C(O)C.[Pd]>[NH2:15][C:11]1[CH:10]=[C:9]([C:3]2[C:4](=[O:8])[N:5]([CH3:7])[CH2:6][C:2]=2[OH:1])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 54707314HCID 54707314, compound

Product 1

HCID 54707315HCID 54707315, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1,5-dihydro-4-hydroxy-N-methyl-3-(3-nitrophenyl)-2H-pyrrol-2-one (1.23 g, 5.3 mmol)in ethanol (70 ml) was hydrogenated at 40 psi using a palladium on carbon catalyst (300 mg, 24% (w /w)) for 30 min. The catalyst was filtered off and the solvent evaporated in vacuo. The residue was azeotroped with toluene (2×30 ml) and then triturated with anhydrous ether (30 ml). The tetramic acid (0.90 g, 83%) was isolated as a yellow solid. 1H NMR (360MHz, D6 -DMSO ) δ2.85 (3H, s), 3.87 (2H, s), 6.37 (1H, dd, J=7 and 1Hz), 6.93 (1H, t, J=8Hz), 7.12 (1H, d, J=8Hz), 7.20 (1H, t, J=2Hz). MS (CI, NH3) 222 (M+NH4 +).

Workup

  1. customfor 30 min
  2. filtrationThe catalyst was filtered off
  3. customthe solvent evaporated in vacuo
  4. customThe residue was azeotroped with toluene (2×30 ml)
  5. customtriturated with anhydrous ether (30 ml)

Sources & evidence

ORD record
ord-26a19701213e4cd0aeff693dd36caefa
Source dataset
uspto-grants-1995_04
Patent number
US05410049

Reaction notes

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