Isonicotinic Acid → 2-Saccharinylmethyl pyridine-4-carboxylate

HRID 864755Notes

Reaction equation

HRID 864755 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:11][N:12]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[S:13]1(=[O:15])=[O:14].C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[N:5]1[CH:6]=[CH:7][C:2]([C:1]([O:9][CH2:11][N:12]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:13]2(=[O:14])=[O:15])=[O:8])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 15225519N-Bromomethylsaccharin

Product 1

HCID 98617952-Saccharinylmethyl pyridine-4-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of isonicotinic acid (0.98 g, 0.008 mol), 2-bromomethylsaccharin (2.11 g, 0.008 mol), triethylamine (0.81 g, 0.008 mol) and xylene (25 ml) were refluxed for 1 hour. The solvent was removed in vacuo and the residue was partitioned between water and methylene chloride. The organic layer was separated and the solvent removed in vacuo. The solid residue was recrystallized from CH3CN to afford 0.9 g (37%) of 2-saccharinylmethyl pyridine-4-carboxylate as a yellow solid, m.p. 145°-146° C.

Workup

  1. temperaturewere refluxed for 1 hour
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and methylene chloride
  4. customThe organic layer was separated
  5. customthe solvent removed in vacuo
  6. customThe solid residue was recrystallized from CH3CN

Sources & evidence

ORD record
ord-6457aa1183e04a4099e7ab2d812163ed
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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