Methyl iodide → HCID 15085977, compound

HRID 1073284Notes

Reaction equation

HRID 1073284 reaction equation
[C:1](#N)C.[NH2:4][C:5]1[C:6]([C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([OH:17])=[O:16])=[CH:12][C:11]([F:18])=[CH:10][CH:9]=2.C(=O)([O-])[O-].[Cs+].[Cs+].CI>O1CCCC1>[CH3:1][O:16][C:15]([C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:18])[CH:12]=2)[N:7]=[C:6]([C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=2)[C:5]=1[NH2:4])=[O:17]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 15085976HCID 15085976, compound

Product 1

HCID 15085977HCID 15085977, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 400 ml of acetonitrile and 40 ml of tetrahydrofuran was added 4.0 g of 3-amino-6-fluoro-2-(4-iodophenyl)-4-quinolinecarboxylic acid and 2.0 g of cesium carbonate. The solution was stirred for 1 hour and 0.84 ml of methyl iodide was added. After stirring for an additional 12 hours, the volatiles were removed in vacuo and the residue dissolved in methylene chloride and ethyl acetate. The insoluble solids were removed by filtration and the volatiles removed from the filtrate in vacuo. The yellow solid obtained was recrystallized from methylene chloride, giving 3.45 g of the desired compound as yellow crystals, mp 223°-225° C.

Workup

  1. stirringAfter stirring for an additional 12 hours
  2. customthe volatiles were removed in vacuo
  3. dissolutionthe residue dissolved in methylene chloride
  4. customThe insoluble solids were removed by filtration
  5. customthe volatiles removed from the filtrate in vacuo
  6. customThe yellow solid obtained
  7. customwas recrystallized from methylene chloride

Sources & evidence

ORD record
ord-2755593bedd64ff888bbb5b31f6b142a
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

Loading…