Ammonium Chloride → HCID 86692255, compound

HRID 1469768Notes

Reaction equation

HRID 1469768 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[C:9]2[NH: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-]>C(O)C.O.[Fe]>[F:24][C:21]([F:22])([F:23])[C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:9]2[C:10]3[CH:11]=[CH:12][CH:13]=[C:4]([NH2:1])[C:5]=3[CH:6]=[CH:7][N:8]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 71678546HCID 71678546, compound

Product 1

HCID 86692255HCID 86692255, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

The title compound was prepared following the procedure described in Intermediate-1, step-3 using 5-nitro-N-(4-(trifluoromethyl)phenyl)isoquinolin-1-amine (750 mg, 2.25 mmol), iron powder (1.26 g, 22.5 mmol), and NH4Cl (963 mg, 18.0 mmol) in EtOH—H2O (5:2, 7 mL) to afford 260 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 9.27 (s, 1H), 8.09 (d, J=9.0 Hz, 2H), 7.94 (d, J=6.0 Hz, 1H), 7.64 (m, 3H), 7.44 (d, J=5.7 Hz, 1H), 7.33 (t, J=7.8 Hz, 1H), 6.87 (d, J=7.8 Hz, 1H), 5.87 (br s, 2H); MS (m/z): 304.28 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-19f4b8e077e8444c9a8f2725a5067398
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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