Potassium Carbonate → HCID 59596629, compound

HRID 2264893Notes

Reaction equation

HRID 2264893 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[CH:4][CH:3]=1.Cl.[CH2:14]([O:16][C:17](=[O:21])[CH2:18][NH:19][CH3:20])[CH3:15].[H-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([O:16][C:17]([C:18]1[N:19]([CH3:20])[C:2]2[CH:3]=[CH:4][N:5]=[CH:6][C:7]=2[C:8]=1[OH:10])=[O:21])[CH3:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 14116704Ethyl 4-chloropyridine-3-carboxylate

Product 1

HCID 59596629HCID 59596629, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of ethyl 4-chloro-nicotinate (2.05 g, 11.0 mmol) and sarcosine ethyl ester hydrochloride (4.75 g, 30.9 mmol) in anhydrous DMF (40 ml), under an argon atmosphere, was added sodium hydride (59.6 mmol, 60% in dispersion oil, 2.39 g) in portions over 20 minutes. On complete addition the mixture was heated at 80° C. for 1.5 hours. Potassium carbonate (1.52 g, 11.0 mmol) was then added and the mixture heated for a further 2 hours. The reaction mixture was then quenched by the addition of water (50 ml) and subsequently concentrated to provide a residue. The residue was partitioned between ethyl acetate (100 ml) and water (100 ml). The layers were separated, the aqueous phase was cooled to 0° C. and the pH adjusted to 7 by the addition of concentrated HCl. The aqueous phase was aged overnight and the resulting precipitate was filtered, washed with water and dried under vacuum at 60° C. to give a white solid (700 mg, 15%). LCMS (method B): RT=1.82 min, M+H+=221.

Workup

  1. additionOn complete addition the mixture
  2. temperaturethe mixture heated for a further 2 hours
  3. customThe reaction mixture was then quenched by the addition of water (50 ml)
  4. concentrationsubsequently concentrated
  5. customto provide a residue
  6. customThe residue was partitioned between ethyl acetate (100 ml) and water (100 ml)
  7. customThe layers were separated
  8. temperaturethe aqueous phase was cooled to 0° C.
  9. additionthe pH adjusted to 7 by the addition of concentrated HCl
  10. filtrationthe resulting precipitate was filtered
  11. washwashed with water
  12. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-52fc868fbe054400bb9e2f030b897300
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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