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

HRID 612246Notes

Reaction equation

HRID 612246 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. temperatureto reflux under N2
  2. customremoved
  3. temperatureheat
  4. customazeotroped with ethanol
  5. customSlurried residue with hexane, collected solids
  6. washwashed with water
  7. dissolutionDissolved in ethyl acetate
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-6d99d4b71f354f0c96e46dbf4eea91a0
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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