Hydrochloric Acid → 5-Bromo-2-methylpyridin-3-amine

HRID 1892589Notes

Reaction equation

HRID 1892589 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5]([CH3:8])=[N:6][CH:7]=1.Cl>[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([CH3:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 250672665-Bromo-2-methyl-3-nitropyridine

Product 1

HCID 219640965-Bromo-2-methylpyridin-3-amine

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To a solution of 5-bromo-2-methyl-3-nitropyridine (13.8 g, 63.9 mmol) in industrial methylated spirit (330 mL) at 40° C. was added iron powder (20 g) (portionwise to avoid clumping) followed by concentrated aqueous hydrochloric acid (5 mL). The dark brown mixture was stirred vigorously at reflux for 2 hours and then cooled and filtered through Celite® (which was washed with 1 L of industrial methylated spirit). The solvent was then removed in vacuo and the residue taken up in ethyl acetate (200 mL) and washed with a saturated aqueous solution of sodium bicarbonate (200 mL), dried over magnesium sulfate and solvent removed in vacuo to give 5-bromo-2-methylpyridin-3-amine as an orange solid, (10.7 g, 57.5 mmol, 89.9%) 1HNMR (400 MHz, CDCl3): δ ppm 7.91 (s, 1H), 7.00 (s, 1H), 3.75 (br. s, 2H), 2.25 (5, 3H).

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturecooled
  3. filtrationfiltered through Celite® (which was washed with 1 L of industrial methylated spirit)
  4. customThe solvent was then removed in vacuo
  5. washwashed with a saturated aqueous solution of sodium bicarbonate (200 mL)
  6. dry with materialdried over magnesium sulfate and solvent
  7. customremoved in vacuo

Sources & evidence

ORD record
ord-b088101a128b401ebd1729d29983ab40
Source dataset
uspto-grants-2013_08
Patent number
US08507681B2

Reaction notes

Loading…