Ammonium Chloride → 4-(3-(Trifluoromethyl)phenoxy)quinolin-8-amine

HRID 1469735Notes

Reaction equation

HRID 1469735 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[F:24][C:21]([F:22])([F:23])[C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][C:9]1[C:8]2[C:13](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=2)[N:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 866922328-Nitro-4-(3-(trifluoromethyl)phenoxy)quinoline

Product 1

HCID 716780474-(3-(Trifluoromethyl)phenoxy)quinolin-8-amineYield 82.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 8-nitro-4-(3-(trifluoromethyl)phenoxy)quinoline (200 mg, 0.60 mmol) and iron powder (267 mg, 4.77 mmol) in EtOH (3 mL) was added a solution of NH4Cl (312 mg, 5.89 mmol) in water (2 mL) and the reaction mixture was heated at reflux for 2 h. Then the reaction mixture was cooled to rt and filtered. The filtrate was concentrated and the concentrate was dissolved in CHCl3. The organic layer was washed with an aq. saturated solution of NaHCO3 and brine. The organic layer was separated, dried, filtered and concentrated to afford 150 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.58 (d, J=4.8 Hz, 1H), 7.77-7.65 (m, 3H), 7.55 (d, J=7.8 Hz, 1H), 7.32 (m, 2H), 6.64 (m, 1H), 6.71 (d, J=4.8 Hz, 1H), 6.00 (br s, 2H); MS (m/z): 305.22 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe concentrate was dissolved in CHCl3
  6. washThe organic layer was washed with an aq. saturated solution of NaHCO3 and brine
  7. customThe organic layer was separated
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-661d34a653f44903bbc1c0178e57c89d
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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