Ammonium Chloride → 4-ethenyl-3,4-dihydro-1H-isochromen-8-amine

HRID 2173269Notes

Reaction equation

HRID 2173269 reaction equation
[CH:1]([CH:3]1[C:12]2[C:7](=[C:8]([N+:13]([O-])=O)[CH:9]=[CH:10][CH:11]=2)[CH2:6][O:5][CH2:4]1)=[CH2:2].[NH4+].[Cl-]>CCO.O.[Fe]>[CH:1]([CH:3]1[C:12]2[C:7](=[C:8]([NH2:13])[CH:9]=[CH:10][CH:11]=2)[CH2:6][O:5][CH2:4]1)=[CH2:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 675178764-ethenyl-8-nitro-3,4-dihydro-1H-isochromene

Product 1

HCID 675183344-ethenyl-3,4-dihydro-1H-isochromen-8-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-ethenyl-8-nitro-3,4-dihydro-1H-isochromene (630 mg, 3.07 mmol), Fe (860 mg, 15.3 mmol) and NH4Cl (1.642 g, 30.7 mmol) in EtOH/H2O (2:1, 40 mL) was stirred at reflux under N2 protection for 2 h. The mixture was filtered, and the filtrate was evaporated to give 4-ethenyl-3,4-dihydro-1H-isochromen-8-amine. 1H-NMR (400 MHz, DMSO) δ 6.88 (t, J=8.0 Hz, 1H), 6.47 (d, J=8.0 Hz, 1H), 6.34 (d, J=8.0 Hz, 1H), 5.74˜5.83 (m, 1H), 5.03˜5.17 (m, 2H), 4.46 (s, 2H), 3.78˜3.82 (m, 1H), 3.61˜3.65 (m, 1H), 3.36˜3.38 (m, 1H).

Workup

  1. temperatureat reflux under N2 protection for 2 h
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-727edf3635e0458ca5708f7fe2e873ed
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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