3-(Trifluoromethoxy)aniline → HCID 22466532, compound

HRID 1935159Notes

Reaction equation

HRID 1935159 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[F:17][C:18]([F:28])([F:27])[O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23]>C(O)C>[F:17][C:18]([F:27])([F:28])[O:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 737533-(Trifluoromethoxy)anilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 22466532HCID 22466532, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-3-quinolinecarbonitrile, 200 ml ethanol, and 3.4 ml (25.3 mmol) 3-trifluoromethoxyaniline was heated to reflux. At 5 hours, removed heat and made basic with saturated sodium bicarbonate. Stripped solvents, slurried residue with hexane, collected, and washed with water. Dissolved in ethyl acetate, stirred with Darco, filtered, stripped solvent, and dried in vacuo, giving 4.537 g of yellow-orange solid: mass spectrum (electrospray m/e): M+H=374.8.

Workup

  1. temperaturewas heated to reflux
  2. customremoved
  3. temperatureheat
  4. customcollected
  5. washwashed with water
  6. dissolutionDissolved in ethyl acetate
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-332e9f0a42ba46258af3dc0a9e91a507
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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