Potassium Hydroxide → Methyl 2,4-dichloropyridine-3-carboxylate

HRID 1170891Notes

Reaction equation

HRID 1170891 reaction equation
N([CH2:3]NC(N)=O)=O.[OH-].[K+].[Cl:10][C:11]1[N:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:12]=1[C:13]([OH:15])=[O:14]>C(OCC)C.CO>[Cl:10][C:11]1[N:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:12]=1[C:13]([O:15][CH3:3])=[O:14]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 104823Urea, (nitrosomethyl)-HCID 105838872,4-Dichloronicotinic Acid

Product 1

HCID 27282740Methyl 2,4-dichloropyridine-3-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Nitrosomethyl urea (8 g, 78.16 mmol), taken in diethyl ether (30 ml) was cooled to 0° C. and 25% aqueous KOH solution was added slowly under cooling. The ether layer was collected, dried over KOH and added dropwise to a stirring solution of 2,4-Dichloronicotinic acid (3 g, 15.62 mmol) in methanol (5 mL) at 0° C. The reaction mixture was allowed to come to room temperature within 1 hour. The organic solvent was removed under reduced pressure and the crude residue was purified by column chromatography (5-10% EtOAc in hexane) to obtain the pure methyl 2,4-dichloronicotinate (3.00 g, 99%) as colorless oil. 1H NMR (400 MHz, CDCl3): δ 8.34 (d, J=5.3 Hz, 1H), 7.33 (d, J=5.4 Hz, 1H), 3.99 (s, 3H).

Workup

  1. temperatureunder cooling
  2. customThe ether layer was collected
  3. dry with materialdried over KOH
  4. customThe organic solvent was removed under reduced pressure
  5. customthe crude residue was purified by column chromatography (5-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-aaaf458e7a7b4af19c4f2fac006f7827
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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