HCID 21467102, compound → HCID 21467093, compound

HRID 2379367Notes

Reaction equation

HRID 2379367 reaction equation
[C:1]([O:4][C:5]1[C:10](=[O:11])[CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=2)[O:7][CH:6]=1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][C:5]1[C:10](=[O:11])[CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=2)[O:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 21467102HCID 21467102, compound

Product 1

HCID 21467093HCID 21467093, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Acetoxy-6-(3-nitrophenyl)-4-pyrone (1.80 g, 6.5 mmol) was dissolved in methanol (50 ml) and hydrogenated at 10 psi for 1 h, using 10% palladium on carbon catalyst (0.2 g, 11% (w/w)). The reaction mixture was then filtered through "hyflo" and the filtrate evaporated in vacuo. The residue was recrystallised from ethyl acetate:hexane (2:1) to afford the desired product (1.20 g, 75%) as a beige solid. mp 127°-129° C. 1H NMR (360 MHz, CDCl3) δ 2.35 (3H, s), 3.85 (2H, brs), 6.81 (1H, dd, J=8.0 and 1.0 Hz), 6.84 (1H, s), 7.02 (1H, dd, J=1.0 and 1.0 Hz), 7.11 (1H, brd, J=8.0 Hz), 7.25 (1H, dd, J=8.0 and 8.0 Hz), 7.98 (1H, s).

Workup

  1. filtrationThe reaction mixture was then filtered through "hyflo"
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was recrystallised from ethyl acetate:hexane (2:1)

Sources & evidence

ORD record
ord-cb10afaeeaae483c83b6e5026eea005b
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

Loading…