Sodium Hydroxide → 3-Amino-5-bromo-2-chloropyridine

HRID 1952307Notes

Reaction equation

HRID 1952307 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5]([Cl:8])=[N:6][CH:7]=1.O.O.Cl[Sn]Cl.[OH-].[Na+]>Cl>[NH2:9][C:4]1[C:5]([Cl:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 218583543-Amino-5-bromo-2-chloropyridineYield 89%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred suspension of 5-bromo-2-chloro-3-nitropyridine (20.0 g, 84.2 mMol) in conc. HCl (90 mL) was added SnCl2.2H2O (60.0 g, 266 mMol) portionwise over 2 h. (The reaction got very warm to the touch.) The reaction was stirred at RT for 18 h, poured onto ice, and basified with aq. 6 N NaOH (300 mL). The resultant slurry was filtered, washed with H2O, and dried under vacuum to give the title compound (15.53 g, 89%) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.66 (d, J=2.3 Hz, 1H), 7.30 (d, J=2.3 Hz, 1H), 5.90 (br.s., 2 H); MS (ES) m/e 206.7 (M+H)+.

Workup

  1. temperaturegot very warm to the touch
  2. additionpoured onto ice
  3. filtrationThe resultant slurry was filtered
  4. washwashed with H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a100a53a018b4086b903ca808f9caf31
Source dataset
uspto-grants-2013_03
Patent number
US08404837B2

Reaction notes

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