Sulfuric Acid → HCID 58703142, compound

HRID 518319Notes

Reaction equation

HRID 518319 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH3:9])[C:5](N)=[N:6][CH:7]=1.[OH:11]S(O)(=O)=O.N([O-])=O.[Na+]>O>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH3:9])[C:5](=[O:11])[NH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 70103075-Bromo-3,4-dimethylpyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 58703142HCID 58703142, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
31 °C

Procedure

To a mixture of 5-bromo-3,4-dimethylpyridin-2-amine (0.6 g, 3.0 mmol) and H2SO4 (98%, 1.62 mL) and H2O (18 mL) is added a solution of NaNO2 (243.6 mg, 4.2 mmol) in H2O (1.6 mL) drop-wise at 0° C. Then, it was stirred at 31° C. for 30 minutes and filtered. The resulting solid is washed with water to provide the title compound (375.0 mg, 62%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.48 (s, 1H), 2.32 (s, 3H), 2.19 (s, 3H). LCMS (M+H)+ 202.

Workup

  1. filtrationfiltered
  2. washThe resulting solid is washed with water

Sources & evidence

ORD record
ord-2c8b8ef3b0db469ab8a6800971bcdc13
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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