Hydrochloric Acid → 6-Aminopyridine-2-carboxylic acid

HRID 2120069Notes

Reaction equation

HRID 2120069 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([OH:13])=[O:12])[N:6]=1)(=O)C.Cl>[OH-].[Na+]>[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([OH:13])=[O:12])[N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 8246406-Acetamidopicolinic acid

Product 1

HCID 3516526-Aminopyridine-2-carboxylic acidYield 76.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-acetylaminopyridine-6-carboxylic acid (4.1 g) in 2.5 N NaOH (36.5 ml) was heated at 80° C. for 1.5 hours, under nitrogen atmosphere. The resulting solution was cooled and acidified with cold 3N HCl. The precipitate obtained was filtered, washed successively with water and acetonitrile. The resulting white solid was dried under vacuum to afford 2-aminopyridine-6-carboxylic acid (2.4 g, 76% yield). 1H-NMR (DMSO-d6) δ 7.57 (t, 1H, J=8.1 Hz), 7.14 (d, 1H, J=7.2 Hz), 6.67 (1H, J=8.1 Hz), 6.51 (br, 2H); FAB MS m/z 139 (M+H).

Workup

  1. temperatureThe resulting solution was cooled
  2. customThe precipitate obtained
  3. filtrationwas filtered
  4. washwashed successively with water and acetonitrile
  5. customThe resulting white solid was dried under vacuum

Sources & evidence

ORD record
ord-ea5c1a960bcc40ed87bdba7097969c77
Source dataset
uspto-grants-2004_02
Patent number
US06689754B1

Reaction notes

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