Hydrochloric Acid → 5-Bromo-6-methyl-2,3-pyridinediamine

HRID 2294888Notes

Reaction equation

HRID 2294888 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[N:4][C:5]([NH2:11])=[C:6]([N+:8]([O-])=O)[CH:7]=1.Cl>C(O)C.O.[Fe]>[Br:1][C:2]1[C:3]([CH3:12])=[N:4][C:5]([NH2:11])=[C:6]([NH2:8])[CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 1119015-Bromo-6-methyl-3-nitropyridine-2-amine

Product 1

HCID 1010225-Bromo-6-methyl-2,3-pyridinediamineYield 98.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7.7 g (33.2 mmole) of the compound obtained in step 2 was dissolved in a mixture of 27 ml of ethanol and 7 ml of water and to the resulting solution were added 20 g (0.36 mole) of iron powder and 0.33 ml of conc. hydrochloric acid. The resultant was refluxed with stirring for 1 hour, filtered through Cellite to remove the remaining iron powder and washed with ethanol (50 ml×3). The filtrate was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. The resultant was passed through silica gel and concentrated under reduced pressure to obtain 6.6 g of the title compound (yield 98%).

Workup

  1. temperatureThe resultant was refluxed
  2. filtrationfiltered through Cellite
  3. customto remove the remaining iron powder
  4. washwashed with ethanol (50 ml×3)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5907446808fe46b998f5b4f7e8a588dd
Source dataset
uspto-grants-1997_11
Patent number
US05691348

Reaction notes

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