Iodoethane → HCID 12795490, compound

HRID 2286205Notes

Reaction equation

HRID 2286205 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[CH3:12])[NH:8][CH:7]=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2=[O:19].[H-].[Na+].[H][H].[CH2:24](I)[CH3:25]>CN(C)C=O.O>[CH2:24]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([CH3:12])[C:10]=2[F:13])[C:5](=[O:19])[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]1)[CH3:25]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12795489HCID 12795489, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12795490HCID 12795490, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.67 g of ethyl 6,8-difluoro-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate are suspended in 50 ml of dimethylformamide, and 0.46 g of 66% sodium hydride are added thereto. The suspension is stirred at room temperature until it ceases to release hydrogen gas. 3.12 g of ethyl iodide are added to the suspension, and said suspension is stirred at room temperature for 24 hours and then at 50° to 60° C. for 3 hours. The reaction mixture is condensed to dryness, and water is added to the residue. After stirring the aqueous mixture, insoluble materials are collected by filtration, washed with isopropanol and then dried. 1.95 g of ethyl 1-ethyl-6,8-difluoro-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate are thereby obtained as crystalline powder. Yield: 66%

Workup

  1. stirringis stirred at room temperature for 24 hours
  2. additionis added to the residue
  3. stirringAfter stirring the aqueous mixture, insoluble materials
  4. filtrationare collected by filtration
  5. washwashed with isopropanol
  6. customdried

Sources & evidence

ORD record
ord-12caaa98c66b48239b68d6730ad82d9d
Source dataset
uspto-grants-1982_04
Patent number
US04327101

Reaction notes

Loading…