Ammonium Chloride → HCID 71678550, compound

HRID 1469777Notes

Reaction equation

HRID 1469777 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][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[F:24][C:21]([F:22])([F:23])[C:18]1[CH:19]=[CH:20][C:15]([O:14][C:9]2[C:8]3[C:13](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=3)[N:12]=[CH:11][CH:10]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 71678380HCID 71678380, compound

Product 1

HCID 71678550HCID 71678550, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared following the procedure described in Intermediate-11, step-4 using 8-nitro-4-(4-(trifluoromethyl)phenoxy)quinoline (200 mg, 0.59 mmol), iron powder (335 mg, 5.98 mmol), and NH4Cl (260 mg, 4.70 mmol) in EtOH (5 mL) and water (1 mL) to afford 126 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.60 (d, J=4.8 Hz, 1H), 7.85 (d, J=8.7 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 7.31 (d, J=7.8 Hz, 1H), 7.25 (d, J=7.8 Hz, 1H), 6.92 (d, J=7.2 Hz, 1H), 6.85 (d, J=5.4 Hz, 1H), 6.01 (s, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e89661de57774272ad5e1def641698de
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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