Sodium hydride → Sodium 2-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinecarboxylate

HRID 364359

Reaction equation

HRID 364359 reaction equation
[H-].[Na+:2].[CH3:3][N:4]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5]1.Cl[C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C([O-])(=O)C.[Na+]>CS(C)=O>[CH3:3][N:4]1[CH2:8][CH2:7][CH:6]([O:9][C:11]2[C:12]([C:13]([O-:15])=[O:14])=[CH:16][CH:17]=[CH:18][N:19]=2)[CH2:5]1.[Na+:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 762582-Chloronicotinic acidHCID 930741-Methyl-3-pyrrolidinolHCID 517045Sodium Acetate

Product 1

HCID 23718944Sodium 2-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred suspension of 6.4 g (0.13 mole) of 50% sodium hydride (mineral oil) in 50 ml of dimethylsulfoxide was added dropwise 6.4 g (0.063 mole) of 1-methyl-3-pyrrolidinol. During addition, the temperature rose from 25° C. to 31° C. After 10 minutes, a solution of 10 g (0.063 mole) of 2-chloronicotinic acid in 50 ml of dimethylsulfoxide was added dropwise causing the temperature to rise. When the temperature reached 55° C., it was maintained there by the intermittent use of an ice bath until addition was complete. The mixture was then heated to 55°-60° C. for 1.5 hr., cooled and filtered. The filter cake was suspended in 100 ml of ethyl acetate and filtered. The solid was recrystallized from ethyl acetatemethanol. Yield of product was 5 g., dec. 240° C. The NMR analysis showed that the compound contained 1/3 mole of sodium acetate as impurity.

Workup

  1. additionDuring addition
  2. customrose from 25° C. to 31° C
  3. customreached 55° C.
  4. temperatureit was maintained there by the intermittent use of an ice bath until addition
  5. temperatureThe mixture was then heated to 55°-60° C. for 1.5 hr
  6. temperature, cooled
  7. filtrationfiltered
  8. filtrationfiltered
  9. customThe solid was recrystallized from ethyl acetatemethanol
  10. custom240° C

Sources & evidence

ORD record
ord-21a9e087d7e444d4bbe9acd918f09fe6
Source dataset
uspto-grants-1986_08
Patent number
US04604388

Linked notes

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