4-Chloro-2-fluoroaniline → HCID 22466695, compound

HRID 1935155Notes

Reaction equation

HRID 1935155 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([F:27])[CH:21]=1>C(O)C>[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:17]#[N:18])=[C:22]([F:27])[CH:21]=1

Participants

4

Reactant 2

HCID 938984-Chloro-2-fluoroanilineHCID 111399754-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

Product 1

HCID 22466695HCID 22466695, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.017 g (19.0 mmol) 4-chloro-7-methoxy-6-nitro-3-quinolinecarbonitrile, 250 ml ethanol, and 2.55 ml 22.8 mmol) 4-chloro-2-fluoroaniline was heated to reflux under N2. At 3.5 hours, removed heat and made basic with saturated sodium bicarbonate. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane, collected solids, and washed with water. Dissolved in ethyl acetate, stirred with Darco, filtered, stripped solvent, and dried in vacuo, giving 6.54 g of yellow solid: mass spectrum (electrospray m/e): M+H=372.8, 374.8.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customremoved
  4. temperatureheat
  5. customazeotroped with ethanol
  6. customSlurried residue with hexane, collected solids
  7. washwashed with water
  8. dissolutionDissolved in ethyl acetate
  9. filtrationfiltered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-f821368e5fdd497d9c35b05a97db15b1
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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