Sodium Hydroxide → Pranoprofen

HRID 1579451

Reaction equation

HRID 1579451 reaction equation
Cl[C:2]([C:7]1[CH:8]=[CH:9][C:10]2[O:19][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH2:12][C:11]=2[CH:20]=1)([CH3:6])[C:3]([OH:5])=[O:4].[OH-].[Na+]>[Ni].[H][H]>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]2[CH2:12][C:11]3[CH:20]=[C:7]([CH:2]([CH3:6])[C:3]([OH:5])=[O:4])[CH:8]=[CH:9][C:10]=3[O:19][C:14]=12

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 215685142-chloro-2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid

Product 1

HCID 4888PranoprofenYield 58.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

A mixture of 2.9 g of 2-chloro-2-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid, 40 ml of 0.5 N aqueous sodium hydroxide solution and 1 g of Raney nickel is stirred in a hydrogen stream at ordinary pressure and temperature, until absorption of 230 ml of hydrogen is attained. The RAney nickel is then filtered off, and the filtrate is neutralized with hydrochloric acid. The crystalline precipitate is filtered off, washed with water, and recrystallized from aqueous dioxane to give 1.5 g of 2-(5H-[1]benzopyrano-[2,3-b]pyridin-7-yl)propionic acid melting at 183°-184°C.

Workup

  1. filtrationThe RAney nickel is then filtered off
  2. filtrationThe crystalline precipitate is filtered off
  3. washwashed with water
  4. customrecrystallized from aqueous dioxane

Sources & evidence

ORD record
ord-e74532c36a8742fbac5be2082ad23742
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Linked notes

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