Chloroacetic Acid → (2-Imino-2H-pyridin-1-yl)-acetic acid

HRID 42259Notes

Reaction equation

HRID 42259 reaction equation
Cl[CH2:2][C:3]([OH:5])=[O:4].C(N(CC)CC)C.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>O.C(O)C>[NH:13]=[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]1[CH2:2][C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 8471TriethylamineHCID 104392-Aminopyridine

Product 1

HCID 10997222(2-Imino-2H-pyridin-1-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

In a 100 mL round bottom flask, 2-chloroacetic acid (10 g, 106 mmol) in water (16.3 mL) was treated with triethylamine (16.67 mL, 120 mmol) dropwise over about 6 minutes. After stirring the reaction at ambient temperature for 10 minutes, 2-aminopyridine (11.76 g, 125 mmol) was added and the mixture was heated at 90° C. for 5 hours. The reaction mixture was cooled to ambient temperature and diluted with ethanol (11 mL). The resulting suspension was stirred in an ice bath for 1 hour and filtered. The solid collected was washed with about 30 mL cold ethanol and dried under vacuum to a constant weight to provide the title compound. MS (DCI+) m/e 152.9 (M+H)+.

Workup

  1. customthe reaction at ambient temperature for 10 minutes
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. stirringThe resulting suspension was stirred in an ice bath for 1 hour
  4. filtrationfiltered
  5. customThe solid collected
  6. washwas washed with about 30 mL cold ethanol
  7. customdried under vacuum to a constant weight

Sources & evidence

ORD record
ord-020898a18a2f4774a64811a561de6c96
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Reaction notes

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