Stannous chloride dihydrate → HCID 59631320, compound

HRID 1431444Notes

Reaction equation

HRID 1431444 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][C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[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][C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 59631269HCID 59631269, compound

Product 1

HCID 59631320HCID 59631320, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
65 °C

Procedure

To a stirred mixture of 2,5-bis(2-methoxyphenyl)-3-nitropyridine (97.3 mg, 0.29 mmol) in EtOAc (5.0 mL) was added tin(II) chloride dihydrate (0.33 g, 1.45 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 65° C. After 2 h, the reaction was cooled to rt and diluted with EtOAc, then washed with 1M NaOH (15 mL), water (15 mL), and brine (15 mL). After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was identified as mostly 2,5-bis(2-methoxyphenyl)-3-pyridinamine. Mass Spectrum (pos.) m/e: 307.1 (M+1).

Workup

  1. additionUpon complete addition of the reducing agent
  2. temperaturethe reaction was cooled to rt
  3. washwashed with 1M NaOH (15 mL), water (15 mL), and brine (15 mL)
  4. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  5. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f0223a174eee473c9053e1a452a15882
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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