Hydrochloric Acid → HCID 21190152, compound

HRID 619427Notes

Reaction equation

[C:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15](O)=[O:16])[N:10]3[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>>[C:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[N:10]3[CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 4311764Sodium borohydride

HCID 91466742-Phenylimidazo[1,2-a]pyridine-5-carboxylic acid

Product 1

HCID 21190152HCID 21190152, compoundYield 52%

Procedure

To a solution of 3.14 g (11.79 mmol) of ethyl ester of 2-phenylimidazo[1,2-a]pyridine-5-carboxylic acid was added, under ice-cooling, 1.34 g (35.37 mmol) of sodium borohydride. The mixture was stirred for 3 hours under ice-cooling. The reaction mixture was poured into 150 ml of ice-water, which was sufficiently blended. To the mixture was added 12N HCl until the pH reached 2. This solution was stirred for two hours at room temperature, which was neutralized with a 6N aqueous solution of NaOH. The solvent was then completely distilled off under reduced pressure. To the residue was added 200 ml of methanol. The mixture was sufficiently blended, then insolubles were filtered off. The solvent was distilled off under reduced pressure to leave 1.37 g of a crude product (52.0%, white solid). This crude product was used in the subsequent reaction without purification.

Workup

temperaturecooling
temperaturecooling
stirringThis solution was stirred for two hours at room temperature
distillationThe solvent was then completely distilled off under reduced pressure
additionTo the residue was added 200 ml of methanol
filtrationinsolubles were filtered off
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-ff7ce2c8fef0444eae7f173e4d12dee1
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05958942

Reaction notes

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