Potassium Carbonate → Methyl-(3-methyl-butyl)-(5-nitro-pyridin-2-yl)-amine

HRID 2236204Notes

Reaction equation

HRID 2236204 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][NH:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:11][N:12]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 521020N,3-Dimethyl-1-butanamine

Product 1

HCID 59301378Methyl-(3-methyl-butyl)-(5-nitro-pyridin-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-5-nitropyridine (158 mg, 1 mmol), N-methylisoamylamine (101 mg, 1 mmol), and finely ground potassium carbonate (419 mg, 3 mmol) were heated to 80° C. in 10 mL anhydrous DMF for 3.5 hrs. The mixture was diluted with EtOAc, extracted with H2O and dried over MgSO4. The EtOAc layer was filtered, evaporated to dryness to yield 220 mg. ES-MS calcd for C11H17N3O2 (m/e) 223.28, obsd 224.1 (M+H).

Workup

  1. extractionextracted with H2O
  2. dry with materialdried over MgSO4
  3. filtrationThe EtOAc layer was filtered
  4. customevaporated to dryness
  5. customto yield 220 mg

Sources & evidence

ORD record
ord-6f61e8bc14c242cc840f6a3f99bd27f6
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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