Water → HCID 22116137, compound

HRID 1276339Notes

Reaction equation

HRID 1276339 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:3]=1.C([O-])=O.[NH4+].O>C(O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 135979336HCID 135979336, compound

Product 1

HCID 22116137HCID 22116137, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 24.0 g (74.57 mmol) 4-chloro-2-[2-(pyridin-2-yl)vinyl]-phenol in 400 ml ethanol is added 1.0 g palladium on charcoal 10% followed by 23.5 g (373 mmol) ammonium formate. The reaction mixture is then heated in an oil bath at 60° C. for 6 hours under a nitrogen atmosphere. The reaction mixture is filtered through celite, and the filtrate evaporated in vacuo to leave a colorless solid. Distilled water is added to the residue, which is extracted with 500 ml and then 300 ml DCM. The organic extracts were dried using MgSO4 and concentrated in vacuo to give the title compound as a colourless solid (15.81 g, 91%), m.p. 135-137° C. δH (250 MHz, CDCl3) 8.52-8.49 (dd, J=5.8,1.7 Hz, 1H), 7.65 (dt, J=7.8,1.7 Hz, 1H), 7.26-7.17 (m, 2H) 7.11 (d, J=2.6 Hz, 1H), 7.04 (dd, J=8.6, 2.6 Hz, 1H), 6.81 (d, J=8.6 Hz, 1H), 3.31-3.26 (m, 2H), 3.10-3.05 (m, 2H).

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. customthe filtrate evaporated in vacuo
  3. customto leave a colorless solid
  4. extractionis extracted with 500 ml
  5. customThe organic extracts were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7be8904b84cf44948115b4f430ce24e4
Source dataset
uspto-grants-2000_12
Patent number
US06166041

Reaction notes

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