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

HRID 1625967Notes

Reaction equation

HRID 1625967 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[Na+]>Cl>[NH2:9][C:4]1[C:5]([Cl:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 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 5 nCl2.2H2O (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, 1 H), 7.30 (d, J=2.3 Hz, 1 H), 5.90 (br. s., 2H); MS(ES) m/e 206.7 (M+H)+.

Workup

  1. additionwas added 5 nCl2.2H2O (60.0 g, 266 mMol) portionwise over 2 h. (The reaction
  2. temperaturegot very warm to the touch
  3. additionpoured onto ice
  4. filtrationThe resultant slurry was filtered
  5. washwashed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-aab6280d0c4d47abba3d4d4cb5bcdf8d
Source dataset
uspto-grants-2014_07
Patent number
US08785433B2

Reaction notes

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