Glycine → (3-Nitro-pyridin-2-ylamino)-acetic acid

HRID 881046Notes

Reaction equation

HRID 881046 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:17][CH2:18][C:19]([OH:21])=[O:20]>CCO.O>[N+:8]([C:7]1[C:2]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 750GlycineHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 3722651(3-Nitro-pyridin-2-ylamino)-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-3-nitropyridine (5 g, 31.5 mmol) was dissolved in EtOH (125 ml), added potassium carbonate (4.35 g, 31.5 mmol) and to this mixture glycine (4.73 g, 6.3 mmol) in 25 ml water was added and refluxed for overnight. The reaction mixture cooled to 0° C. to obtain the solid. Then EtOH was removed on rotavapour and acidified with 2N HCl and solid filtered and dried on vacuum to obtain the title compound quantitatively as a yellow solid.

Workup

  1. temperaturerefluxed for overnight
  2. customto obtain the solid
  3. customThen EtOH was removed on rotavapour
  4. filtrationfiltered
  5. customdried on vacuum

Sources & evidence

ORD record
ord-7c5f66d7d2eb4c84a09dd6c8c4b16539
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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