2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)acrylic acid → Pranoprofen

HRID 1579450Notes

Reaction equation

HRID 1579450 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([C:15](=[CH2:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12.[H][H]>[OH-].[Na+].[Ni]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12

Participants

5

Reactant 2

HCID 215685052-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)acrylic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 4888PranoprofenYield 71.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14798Sodium HydroxideSolvent

Procedure

2.5 g of 2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)acrylic acid is dissolved in 20 ml of 0.5 N aqueous sodium hydroxide soution, and 1 g of Raney nickel is added. The solution is stirred in a hydrogen stream at ordinary pressure and temperature until absorption of 230 ml of hydrogen is attained. The Raney nickel is removed by filtration, and the filtrate is neutralized with hydrochloric acid. The resulting crystalline precipitate is filtered off, washed with water, and recrystallized from aqueous dioxane to give 1.8 g of 2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid melting at 183°-184°C.

Workup

  1. customThe Raney nickel is removed by filtration
  2. filtrationThe resulting crystalline precipitate is filtered off
  3. washwashed with water
  4. customrecrystallized from aqueous dioxane

Sources & evidence

ORD record
ord-92d2f7606fb943c0a1da4ca1852ba987
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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