Ammonium Chloride → HCID 86692246, compound

HRID 1469754Notes

Reaction equation

HRID 1469754 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[C:10]([N+:15]([O-])=O)[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[F:1][C:2]1[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86692245HCID 86692245, compound

Product 1

HCID 86692246HCID 86692246, compoundYield 83.9%

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-(2-fluoro-5-(trifluoromethyl)phenoxy)-8-nitroquinoline (432 mg, 1.22 mmol), iron powder (683 mg, 12.2 mmol), and NH4Cl (517 mg, 9.76 mmol) in EtOH (5 mL) and water (2 mL) to afford 330 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.52 (d, J=5.1 Hz, 1H), 7.94 (d, J=6.6 Hz, 1H), 7.79-7.70 (m, 2H), 7.35 (d, J=6.0 Hz, 2H), 6.91 (d, J=3.6 Hz, 1H), 6.63 (d, J=4.2 Hz, 1H), 5.98 (br s, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-26ac966775ed46d0b234891e9cceb2be
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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