Ammonium Chloride → HCID 86692247, compound

HRID 1469755Notes

Reaction equation

HRID 1469755 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)[CH:8]=[CH:7][N:6]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[F:1][C:2]1[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:18][C:3]=1[O:4][C:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:15])[C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 71678549HCID 71678549, compound

Product 1

HCID 86692247HCID 86692247, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared following the procedure described in Step 3 of Intermediate-1 using 1-(2-fluoro-5-(trifluoromethyl)phenoxy)-5-nitroisoquinoline (320 mg, 0.90 mmol), iron powder (500 mg, 9.09 mmol), and NH4Cl (389 mg, 7.2 mmol) in EtOH (8 mL) and water (2 mL) to afford 230 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 7.89 (d, J=5.7 Hz, 1H), 7.75-7.59 (m, 4H), 7.50 (d, J=7.8 Hz, 1H), 7.40 (t, J=8.1 Hz, 1H), 6.93 (d, J=7.5 Hz, 1H), 6.03 (s, 2H); MS (m/z): 323.28 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-3c56dc45be294763b07a94d62650ceb7
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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