3-(Trifluoromethoxy)aniline → HCID 22466532, compound

HRID 612250Notes

Reaction equation

HRID 612250 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-fe1ee1b7fc6d45878206042d1c630bd1
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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