Water → 8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-acetic acid

HRID 544461Notes

Reaction equation

HRID 544461 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][C:20]#N)=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:22].[Na+].[OH2:24]>C(O)C>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][C:20]([OH:24])=[O:22])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 108137Sch 28080

Product 1

HCID 204589768-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 26 g of 8-benzyloxy-3-cyanomethyl-2-methyl-imidazo[1,2-a]pyridine, 50 ml of 15% sodium hydroxide solution 100 ml of water, and 100 ml of ethanol was heated at reflux for 6 hrs. The reaction mixture was distilled until 100 ml of distillate had been collected. The aqueous portion was washed twice with dichloromethane and then treated with a 6 N hydrochloric acid to pH 6. Filtration afforded 8-benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-acetic acid. 2.0 g of this acid was added to 1 g of lithium aluminium hydride in 100 ml of tetrahydrofuran and was stirred for 5 hrs. at room temperature. The reaction mixture was treated with 1 ml of water, 1 ml of 15% sodium hydroxide solution, then with 3 ml of water. Filtration of salts and evaporation of the filtrate gave the title product after recrystallizationfrom acetonitrile (m.p. 134°-138° C.).

Workup

  1. temperatureat reflux for 6 hrs
  2. distillationThe reaction mixture was distilled until 100 ml of distillate
  3. customhad been collected
  4. washThe aqueous portion was washed twice with dichloromethane
  5. additiontreated with a 6 N hydrochloric acid to pH 6
  6. filtrationFiltration

Sources & evidence

ORD record
ord-8073f8e6a8cb4bd8a5a86640acdfae2f
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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