Ammonium Chloride → HCID 86692222, compound

HRID 1469705Notes

Reaction equation

HRID 1469705 reaction equation
[N+:1]([C:4]1C=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=CN=[C:9]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)([O-])=O.[NH4+:25].[Cl-].[CH3:27][CH2:28]O.O>[Fe]>[F:22][C:21]([F:24])([F:23])[C:17]1[CH:16]=[C:15]([NH:14][C:9]2[C:10]3[CH:11]=[CH:12][N:25]=[C:4]([NH2:1])[C:5]=3[CH:6]=[CH:27][CH:28]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19096565Water ethanolHCID 86692221HCID 86692221, compound

Product 1

HCID 86692222HCID 86692222, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To a solution of 5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-1-amine (1.0 g, 3.0 mmol) in a mixture of EtOH:H2O (8:2, 10 mL) were added iron powder (1.26 g, 4.8 mmol), and NH4Cl (1.6 g, 30.0 mmol). The reaction mass was heated at reflux for 2 h and filtered. The filtrate was concentrated and the residue was purified by column chromatography to afford 0.800 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 9.18 (s, 1H), 8.35 (s, 1H), 8.20 (d, J=7.8 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.52 (t, J=7.8 Hz, 1H), 7.42-7.24 (m, 3H), 6.86 (d, J=7.5 Hz, 1H), 5.84 (s, 2H).

Workup

  1. temperatureThe reaction mass was heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-45898168f4b7469e983c0f051dd67363
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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