Hydrochloric Acid → HCID 12274202, compound

HRID 1579449Notes

Reaction equation

HRID 1579449 reaction equation
Cl.O=[C:3]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[S:6][C:5]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18]([OH:20])=[O:19])=[CH:16][C:4]1=2>O1CCOCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[CH2:3][C:4]3[CH:16]=[C:15]([CH:17]([CH3:21])[C:18]([OH:20])=[O:19])[CH:14]=[CH:13][C:5]=3[S:6][C:7]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12274194HCID 12274194, compound

Product 1

HCID 12274202HCID 12274202, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3.7 g of zinc, 0.22 g of mercuric chloride, 0.22 ml of concentrated hydrochloric acid and 3.7 ml of water is stirred for 5 minutes, and the aqueous solution is removed by decantation. To the zinc amalgam thus obtained are added 6 ml of dioxane and 6 ml of concentrated hydrochloric acid. 1.5 g of 2-(5-oxo-5H-[1]benzothiopyrano[2,3-b]pyridin-7-yl)propionic acid is added to the mixture with stirring at 50°-60°C over a period of about 15 minutes. The whole mixture is stirred at 60°C for 1 hour. The excess zinc is removed by filtration, and the filtrate is evaporated under reduced pressure. The residue is dissolved in water, and the solution is adjusted to pH 2-3 by addition of 10% sodium hydroxide. The resulting crystalline precipitate is filtered off, and recrystallized from aqueous dioxane to give 0.8 g of 2-(5H-[1]benzothiopyrano[2,3-b]pyridin-7-yl)propionic acid as pale yellowish white crystals melting at 203°-204°C.

Workup

  1. stirringThe whole mixture is stirred at 60°C for 1 hour
  2. customThe excess zinc is removed by filtration
  3. customthe filtrate is evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in water
  5. additionthe solution is adjusted to pH 2-3 by addition of 10% sodium hydroxide
  6. filtrationThe resulting crystalline precipitate is filtered off
  7. customrecrystallized from aqueous dioxane

Sources & evidence

ORD record
ord-b8f08279aed64118a292b424fb0baa2e
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

Loading…