Stannous chloride dihydrate → 2-(2-Methoxyphenyl)-3-pyridinamine

HRID 1431442Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][N:10]=1.O.O.[Sn](Cl)Cl>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred mixture of 2-(2-methoxyphenyl)-3-nitropyridine (34.3 mg, 0.15 mmol) in EtOAc (5.0 mL) was added tin(II) chloride dihydrate (0.17 g, 0.76 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 65° C. After 19 h, the reaction was cooled to rt and diluted with EtOAc, then washed with 1M NaOH (10 mL), water (10 mL), and brine (10 mL). After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was identified as mostly 2-(2-Methoxyphenyl)-3-pyridinamine. Mass Spectrum (pos.) m/e: 201.1 (M+1).

Workup

additionUpon complete addition of the reducing agent
temperaturethe reaction was cooled to rt
washwashed with 1M NaOH (10 mL), water (10 mL), and brine (10 mL)
dry with materialAfter drying over anhydrous sodium sulfate and filtration
customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-5191604c958a45af89c3b66510eae792
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

Loading…