HCID 23321888, compound → HCID 13649435, compound

HRID 280226Notes

Reaction equation

HRID 280226 reaction equation
C([O:3][C:4]([CH2:6][S:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[N:17]2[CH:18]=[N:19][CH:20]=[C:16]2[CH:15]=[CH:14][CH:13]=1)=[O:5])C>C(O)C.[OH-].[Na+]>[C:4]([CH2:6][S:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[N:17]2[CH:18]=[N:19][CH:20]=[C:16]2[CH:15]=[CH:14][CH:13]=1)([OH:5])=[O:3]

Participants

4

Reactant 1

HCID 23321888HCID 23321888, compound

Product 1

HCID 13649435HCID 13649435, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-[4-(Ethoxycarbonylmethylthio)butyl]imidazo[1,5-a]pyridine (4.4 g) in 30 ml of ethanol and 61 ml of 1.0N sodium hydroxide is heated under reflux for 3 hours. The ethanol is evaporated, the aqueous is extracted with ethyl acetate (20 ml) and the pH adjusted to 5. The resulting oil is crystallized from ethanol to yield 5-[4-(carboxymethylthio)butyl]imidazo[1,5-a]pyridine, m.p. 124°-126°.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe ethanol is evaporated
  3. extractionthe aqueous is extracted with ethyl acetate (20 ml)
  4. customThe resulting oil is crystallized from ethanol

Sources & evidence

ORD record
ord-ad7cf82c9b2144cabc2bd3a0c43df66c
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

Loading…