Triethylamine → N2,N2-Dimethyl-5-nitropyridine-2,4-diamine

HRID 1160167Notes

Reaction equation

HRID 1160167 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.Cl.[CH3:13][NH:14][CH3:15].C(N(CC)CC)C>C(O)C>[CH3:13][N:14]([CH3:15])[C:4]1[CH:3]=[C:2]([NH2:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 109100582-Chloro-5-nitropyridin-4-amine2×

Product 1

HCID 59515628N2,N2-Dimethyl-5-nitropyridine-2,4-diamineYield 114%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a microwave tube, a solution of 4-amino-2-chloro-5-nitropyridine (prepared as described for compound 9) (200 mg; 1.16 mmol) in ethanol (2 ml) was treated sequentially with dimethylamine hydrochloride (471 mg; 5.78 mmol) and triethylamine (781 μl; 6.96 mmol). The tube was quickly sealed and irradiated in the microwave (CEM Discover, 150 W, 85° C., 10 min). The ethanol was evaporated, dichloromethane (15 ml) was added to dissolve the products, and the solution washed with 1M sodium hydroxide solution (2×10 ml). The organic layer was dried (sodium sulphate), the mixture filtered and the filtrate evaporated to dryness to afford N2,N2-dimethyl-5-nitro-pyridine-2,4-diamine (240 mg, 114%).

Workup

  1. customThe tube was quickly sealed
  2. customirradiated in the microwave (CEM Discover, 150 W, 85° C., 10 min)
  3. customThe ethanol was evaporated
  4. additiondichloromethane (15 ml) was added
  5. dissolutionto dissolve the products
  6. washthe solution washed with 1M sodium hydroxide solution (2×10 ml)
  7. dry with materialThe organic layer was dried (sodium sulphate)
  8. filtrationthe mixture filtered
  9. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-716ce1d8d0d143d6be227f297d4547e0
Source dataset
uspto-grants-2010_10
Patent number
US07816369B2

Reaction notes

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