Hydrochloric Acid → 4-Pyridinecarboxylic acid, 2-[(1-oxopropyl)amino]-, methyl ester

HRID 623550Notes

Reaction equation

HRID 623550 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12](Cl)(=[O:15])[CH2:13][CH3:14].Cl>N1C=CC=CC=1>[C:12]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:15])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 236984Methyl 2-aminopyridine-4-carboxylate

Product 1

HCID 675083644-Pyridinecarboxylic acid, 2-[(1-oxopropyl)amino]-, methyl esterYield 78.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of methyl 2-aminoisonicotinate (1.00 g, 6.57 mmol) in pyridine (22 mL) is added propionyl chloride (0.69 mL, 7.89 mmol) at 0° C. After stirring at 0° C. for 2 hours, the reaction mixture is poured into 2M hydrochloric acid (100 mL) and extracted with ethyl acetate (100 mL). The organic layer is dried over sodium sulfate, and concentrated under reduced pressure to give 1.07 g (78% yield) of the title compound as a yellow solid. This material is used for the next reaction (Step-2) without further purification.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-759ead9dd237439e8221e39e0aeb5275
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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