Hydrochloric Acid → 6-(1-Hydroxyethyl)-2-pyridinecarboxamide

HRID 2379803Notes

Reaction equation

HRID 2379803 reaction equation
[CH3:1][Mg]Br.[CH:4]([C:6]1[N:11]=[C:10]([C:12]([NH2:14])=[O:13])[CH:9]=[CH:8][CH:7]=1)=[O:5].O.Cl>O1CCCC1.C(OCC)(=O)C>[OH:5][CH:4]([C:6]1[N:11]=[C:10]([C:12]([NH2:14])=[O:13])[CH:9]=[CH:8][CH:7]=1)[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18953918HCID 18953918, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 189537876-(1-Hydroxyethyl)-2-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ethereal solution of methyl magnesium bromide (3 mol/l) (546 ml) was added dropwise to a solution of 6-formyl-2-pyridinecarboxamide (61.5 g) in tetrahydrofuran (900 ml) at 0°-13° C. with stirring. After the mixture was stirred at the same temperature for 2 hours and cold water was dropped to the reaction mixture under ice-cooling. To the mixture was added ethyl acetate and adjusted to pH 7 with 6N-hydrochloric acid. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give 6-(1-hydroxyethyl)-2-pyridinecarboxamide (63.2 g) as an oil.

Workup

  1. stirringAfter the mixture was stirred at the same temperature for 2 hours
  2. temperaturecooling
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ae1f1bdbe1bd4524acd096959ceee41e
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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