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

HRID 1469775Notes

Reaction equation

HRID 1469775 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].[NH4+].[Cl-]>CCO.O.[Fe]>[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[C:12]([NH2:17])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:22]([F:25])([F:23])[F:24]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 716778824-(4-Fluoro-3-(trifluoromethyl)phenoxy)-8-nitroquinoline

Product 1

HCID 716780484-(4-Fluoro-3-(trifluoromethyl)phenoxy)quinolin-8-amineYield 64.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared following the procedure described in Intermediate-11, step-4 using 4-(4-fluoro-3-(trifluoromethyl)phenoxy)-8-nitroquinoline (380 mg, 1.07 mmol), iron powder (604 mg, 10.79 mmol), and NH4Cl (461 mg, 8.63 mmol) in EtOH (10 mL) and water (3 mL) to afford 223 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.55 (d, J=4.8 Hz, 1H), 7.75 (d, 1H), 7.67 (d, J=7.5 Hz, 2H), 7.34 (d, J=4.5 Hz, 2H), 6.92 (t, 1H), 6.68 (d, J=4.8 Hz, 1H), 5.98 (s, 2H); MS (m/z): 323.28 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d14b9f7f4d1f4349aad037b9f7c48cb1
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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