HCID 135689355, compound → HCID 135689354, compound

HRID 1654998Notes

Reaction equation

HRID 1654998 reaction equation
[OH:1][C:2]1[CH2:6][S: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>C(O)C.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([C:3]2[C:4](=[O:7])[S:5][CH2:6][C:2]=2[OH:1])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 135689355HCID 135689355, compound

Product 1

HCID 135689354HCID 135689354, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-hydroxy-3-(3-nitrophenyl)-2(5H)-thiophenone (0.36 g, 1.5 mmol) in ethanol (70 ml) was hydrogenated at 40 psi using a palladium on carbon catalyst (200 mg, 55% (w /w)), for 10 min. The catalyst was filtered off and the solvent evaporated in vacuo. The brown residue was triturated with ether (10 ml) and methanol (0.5 ml). 3-(3-Aminophenyl)-4-hydroxy-2(5H)-thiophenone (208 mg, 67%) was isolated as a beige solid. mp 252°-254° C. (dec.). 1H NMR (360MHz, D6 -DMSO) δ3.88 (2H, s), 6.56 (1H, d, J=8Hz), 7.05 (1H, dd, J=8 and 8Hz), 7.13 (1H, d, J =8Hz), 7.21 (1H, s).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated in vacuo
  3. customThe brown residue was triturated with ether (10 ml) and methanol (0.5 ml)

Sources & evidence

ORD record
ord-c407745481204021a07994ed19ffa27f
Source dataset
uspto-grants-1995_04
Patent number
US05410049

Reaction notes

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