Water → HCID 18999059, compound

HRID 2260802Notes

Reaction equation

HRID 2260802 reaction equation
C1CCCCC=1.[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([C:18]1[C:23](Br)=[CH:22][N:21]=[C:20]([O:25][CH3:26])[CH:19]=1)=[O:17])([O-])=O.O.C([O-])(=O)C.[Na+]>C(O)C.[Pd]>[NH2:7][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([C:18]1[CH:23]=[CH:22][N:21]=[C:20]([O:25][CH3:26])[CH:19]=1)=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 8079CyclohexeneHCID 517045Sodium AcetateHCID 18999056HCID 18999056, compound

Product 1

HCID 18999059HCID 18999059, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Cyclohexene (21 ml) was added to a stirred mixture of (2-nitrophenyl)-(5-bromo-2-methoxypyridin-4-yl)methanone (2.16 g) in ethanol (210 ml). A water slurry of 10% palladium on carbon (216 mg) was added followed by sodium acetate (524 mg). The suspension was heated to reflux for 4.5 hours then the mixture was cooled, filtered and evaporated to dryness. The residue was partitioned between dichloromethane and water. The organic layer was separated and the aqueous re-extracted with dichloromethane (twice). The combined organics were washed with water, brine, dried (sodium sulphate) then evaporated to dryness to give the title compound as a yellow solid (1.45 g). mp 82°-86° C. Rf =0.7 in 5% methanol/dichloromethane on silica plates; 1H NMR (360 MHz, CDCl3) δ 3.99 (3H, s), 6.57 (1H, ddd, J=1 and 7 Hz), 6.72 (1H, d, J=7 Hz), 6.86 (1H, s), 7.00 (1H, dd, J=1 and 5 Hz), 7.31 (1H, ddd, J=1 and 7 Hz), 7.37 (1H, dd, J=1 and 7 Hz), 8.26 (1H, d, J=5 Hz), IR (KBr) 3450, 3350, 1640 and 1620 cm-1.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 4.5 hours
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was partitioned between dichloromethane and water
  7. customThe organic layer was separated
  8. extractionthe aqueous re-extracted with dichloromethane (twice)
  9. washThe combined organics were washed with water, brine
  10. dry with materialdried (sodium sulphate)
  11. customthen evaporated to dryness

Sources & evidence

ORD record
ord-2255faa4cbe34063bb74249cbd4c7cb2
Source dataset
uspto-grants-1995_12
Patent number
US05478933

Reaction notes

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