Acetic Acid → HCID 22922184, compound

HRID 2258524Notes

Reaction equation

HRID 2258524 reaction equation
C(C1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[CH:8][C:7]=2[CH:21]=1)=O.[C-:22]#N.[Na+].[C:25]([OH:28])(=[O:27])[CH3:26]>CO.[O-2].[Mn+4].[O-2]>[CH3:22][O:27][C:25]([C:26]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[CH:8][C:7]=2[CH:21]=1)=[O:28]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 22922141HCID 22922141, compound

Product 1

HCID 22922184HCID 22922184, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(5-formylbenzofuran-2-yl)quinoline (0.92 g), manganese (IV) oxide (4.6 g), sodium cyanide (2.2 g) and acetic acid (0.6 ml) in methanol (200 ml) was stirred at ambient temperature for 1.5 hours. The resulting mixture was filtered and filtrate was poured into water (400.ml). The appeared precipitates were collected by filtration and washed with water. The precipitates were subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate (50:1). The fractions containing objected compound were combined and concentrated under reduced pressure to give 2-(5-methoxycarbonylbenzofuran-2-yl)-quinoline (0.48 g).

Workup

  1. filtrationThe resulting mixture was filtered
  2. additionfiltrate was poured into water (400.ml)
  3. customThe appeared precipitates
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. washeluted with a mixture of toluene and ethyl acetate (50:1)
  7. additionThe fractions containing
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-127121b14a2742c6b69d374743a0e22d
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

Loading…