Methanol → HCID 9890688, compound

HRID 864757Notes

Reaction equation

HRID 864757 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:11])[C:7]=1[C:8]([OH:10])=[O:9].C(=O)([O-])[O-].[Cs+].[Cs+].CO.Cl[CH2:21][N:22]1[C:32](=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[CH:34]([CH3:36])[CH3:35])[S:23]1(=[O:25])=[O:24]>CN(C=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:11])[C:7]=1[C:8]([O:10][CH2:21][N:22]1[C:32](=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[CH:34]([CH3:36])[CH3:35])[S:23]1(=[O:24])=[O:25])=[O:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 6057633,5-Dichloroisonicotinic acidHCID 10446001HCID 10446001, compound

Product 1

HCID 9890688HCID 9890688, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3,5-dichloro-4-pyridinecarboxylic acid (0.42 g, 0.002 mol), cesium carbonate (0.36 g, 0.001 mol) and methanol (10 ml) was stirred for 30 minutes. The solvent was removed in vacuo and 2-chloromethyl-4-isopropylsaccharin (0.55 g, 0.002 mol) and DMF (10 ml) were added to the residue. The mixture was heated to 75° C. and stirred for 3 hours. The solvent was removed in vacuo and the residue was partitioned between water/methylene chloride. The organic layer was separated, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was treated with ethereal HCl to afford a white gum which was triturated with Et2O (2X), then acetone. A white solid was obtained which was collected by filtration and dried in high vacuum to afford 0.14 g (15%) of 4-isopropyl-2-saccharinylmethyl 3,5-dichloro-pyridine-4-carboxylate hydrochloride, m.p. 93°-95° C.

Workup

  1. additionwere added to the residue
  2. stirringstirred for 3 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between water/methylene chloride
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. additionThe residue was treated with ethereal HCl
  9. customto afford a white gum which
  10. customwas triturated with Et2O (2X)
  11. customA white solid was obtained which
  12. filtrationwas collected by filtration
  13. customdried in high vacuum

Sources & evidence

ORD record
ord-51cb531e0f59488daf2cc0e57cc44c04
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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