Ammonium Chloride → HCID 86692254, compound

HRID 1469766Notes

Reaction equation

HRID 1469766 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[C:22]2[C:17](=[C:18]([N+:23]([O-])=O)C=[CH:20][CH:21]=2)[CH:16]=CN=1.[NH4+:26].[Cl-].[CH3:28][CH2:29]O.O>[Fe]>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[C:22]2[CH:21]=[CH:20][N:26]=[C:18]([NH2:23])[C:17]=2[CH:16]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19096565Water ethanolHCID 86692253HCID 86692253, compound

Product 1

HCID 86692254HCID 86692254, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

The title compound was prepared following the procedure described in Intermediate-1, step-2 using N-(2-fluoro-4-(trifluoromethyl)phenyl)-5-nitroisoquinolin-1-amine (190 mg, 0.54 mmol), iron powder (303 mg, 5.41 mmol), and NH4Cl (232 mg, 4.32 mmol) in EtOH:H2O (3:1, 4 mL) to afford 120 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.93 (s, 1H), 7.89 (t, J=8.4 Hz, 1H), 7.82 (d, J=6.0 Hz, 1H), 7.64 (d, J=10.8 Hz, 1H), 7.51 (t, 8.4 Hz, 2H), 7.40 (d, J=6.0 Hz, 1H), 7.30 (t, J=7.8 Hz, 1H0, 6.84 (d, J=7.2 Hz, 1H), 5.83 (s, 2H); MS (m/z): 322.33 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b1aca35886964a56b63e10ab58cd0fda
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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