Stannous chloride dihydrate → HCID 59631125, compound

HRID 1431550Notes

Reaction equation

HRID 1431550 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])=[N:6][CH:7]=1.O.O.[Sn](Cl)Cl>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 59631229HCID 59631229, compound

Product 1

HCID 59631125HCID 59631125, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred mixture of 5-bromo-2-(2-methoxyphenyl)-3-nitropyridine (0.2618 g, 0.85 mmol) in EtOAc (10.0 mL) was added tin(II) chloride dihydrate (0.9667 g, 4.28 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 70° C. After 19 h, the reaction was cooled to rt and diluted with EtOAc, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate, filtration, and concentration, the residue was identified as 5-bromo-2-(2-methoxyphenyl)pyridin-3-amine. 1H NMR (500 MHz, CDCl3) δ ppm 8.19 (1H, d, J=2.0 Hz), 7.46 (2H, m), 7.24 (1H, d, J=1.2 Hz), 7.14 (1H, m), 7.03 (1H, d, J=8.3 Hz), 3.84 (3H, s).

Workup

  1. additionUpon complete addition of the reducing agent
  2. temperaturethe reaction was cooled to rt
  3. washwashed with 1M NaOH, water, and brine
  4. dry with materialAfter drying over anhydrous sodium sulfate, filtration, and concentration

Sources & evidence

ORD record
ord-8027ad13602b4c1b99fb16ca802a595d
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…