Water → 6-chloro-N-methyl-3-nitropyridin-2-amine

HRID 1051492Notes

Reaction equation

HRID 1051492 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:18][NH2:19].O>CCO>[Cl:11][C:4]1[N:3]=[C:2]([NH:19][CH3:18])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 10340Sodium CarbonateHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 107500946-chloro-N-methyl-3-nitropyridin-2-amineYield 55.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
18 °C

Procedure

To a solution of 2,6-dichloro-3-nitropyridine (1 g, 7.3 mmol) in EtOH (10 mL) was added Na2CO3 (1.3 g, 12.3 mmol) and MeNH2 at 18° C. The mixture was stirred for 16 hours at 18° C. after which TLC analysis showed the reaction was complete. The reaction mixture was then concentrated to get the crude material which was treated with water (50 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to get yield the crude product which was purified by crystallized with ethanol to give the desired product (780 mg, 55.7%) as a yellow solid. LCMS (m/z): 188.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customto get the crude material which
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto get
  8. customyield the crude product which
  9. customwas purified
  10. customby crystallized with ethanol

Sources & evidence

ORD record
ord-6c2dc5e265cb496a90b6110fc00ebfda
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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