Hydrochloric Acid → 2-(6-Formamidopyridin-2-yl)acetic acid

HRID 2286649Notes

Reaction equation

HRID 2286649 reaction equation
[CH:1]([NH:3][C:4]1[N:9]=[C:8]([CH2:10][C:11]([O:13]CC)=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2].[OH-].[Na+].O.Cl>C(O)C>[CH:1]([NH:3][C:4]1[N:9]=[C:8]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 13060164HCID 13060164, compound

Product 1

HCID 130601732-(6-Formamidopyridin-2-yl)acetic acidYield 65.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 2-(6-formamidopyridin-2-yl)acetate (4.4 g.) in ethanol (44 ml.) was added 2 N sodium hydroxide solution [solvent:water (1 part)+ethanol (4 parts] (15.9 ml.) at 18° to 20° C. over 30 minutes, and then the solution was stirred at room temperature for one hour. After 1 N hydrochloric acid (31.7 ml.) was added to the solution, the solution was concentrated under reduced pressure. The residue was extracted with hot ethyl acetate (500 ml.) and the extract was concentrated under reduced pressure. The residue was washed with ethyl acetate to give 2-(6-formamidopyridin-2-yl)acetic acid (2.5 g.), mp 125° to 126° C. (dec.).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. extractionThe residue was extracted with hot ethyl acetate (500 ml.)
  3. concentrationthe extract was concentrated under reduced pressure
  4. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-bc48ac27dca64be6924a26095ca98a39
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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