Ammonium Chloride → HCID 71678548, compound

HRID 1469772Notes

Reaction equation

HRID 1469772 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)[CH:10]=[CH:9][N: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[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=3[CH:10]=[CH:9][N:8]=2)=[CH:4][C:3]=1[C:22]([F:25])([F:23])[F:24]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86692258HCID 86692258, compound

Product 1

HCID 71678548HCID 71678548, compoundYield 87.2%

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-(4-fluoro-3-(trifluoromethyl)phenoxy)-5-nitroisoquinoline (830 mg, 2.35 mmol), iron powder (1.31 mg, 23.5 mmol), and NH4Cl (1.09 g, 18.8 mmol) in EtOH (8 mL) and water (2 mL) to afford 660 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 7.79 (d, J=6.0 Hz, 1H), 7.71-7.56 (m, 4H), 7.51 (d, J=8.1 Hz, 1H), 7.40 (t, J=8.1 Hz, 1H), 6.94 (d, J=7.2 Hz, 1H), 6.01 (s, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-933325a028ad424faa088689975f59b5
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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