Hydrochloric Acid → HCID 21190273, compound

HRID 1068699Notes

Reaction equation

HRID 1068699 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11](O)=[O:12])[N:6]2[CH:14]=1)[CH3:2].[BH4-].[Na+].Cl.[OH-].[Na+]>>[CH2:1]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][OH:12])[N:6]2[CH:14]=1)[CH3:2]

Participants

5

Procedure

To a solution of 5.29 g (24.24 mmol) of ethyl ester of 2-ethylimidazo[1,2-a]pyridine-5-carboxylic acid was added 2.75 g (72.72 mmol) of sodium borohydride under ice-cooling. The reaction mixture was stirred for 3 hours under ice-cooling. The reaction mixture was then poured into 150 ml of ice-water. The reaction mixture was mixed well, to which was added 12N HCl until the pH of the solution reached 2. This solution was stirred for two hours at room temperature, which was neutralized with a 6N aqueous solution of sodium hydroxide. The solvent was completely distilled off under reduced pressure. To the residue was added 200 ml of methanol. The mixture was mixed well, then insolubles were filtered off. The solvent was distilled off under reduced pressure to give 2.99 g of a crude product (70%, white solid). This crude product was used, without purification, in the subsequent reaction.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionThe reaction mixture was mixed well, to which
  4. stirringThis solution was stirred for two hours at room temperature
  5. distillationThe solvent was completely distilled off under reduced pressure
  6. additionTo the residue was added 200 ml of methanol
  7. additionThe mixture was mixed well
  8. filtrationinsolubles were filtered off
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2fdf143f6aa94b2b8d89658686f9a6fb
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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