Methyl iodide → 3-Methoxy-6-methyl-2-nitropyridine

HRID 2370829Notes

Reaction equation

HRID 2370829 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12]([O-])([O-])=O.[K+].[K+].CI.CCOC(C)=O>CN(C=O)C.CCCCCC>[CH3:12][O:11][C:5]1[C:6]([N+:8]([O-:10])=[O:9])=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 848016-Methyl-2-nitropyridin-3-ol

Product 1

HCID 27279653-Methoxy-6-methyl-2-nitropyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred mixture of 6-methyl-2-nitropyridin-3-ol (5 g, 0.032 mol, Sigma Aldrich) in DMF (50.0 mL) was added K2CO3 (6.72 g, 0.048 mol, S.d.fine chemicals, India). The reaction mixture was stirred for 30 min at room temperature. MeI (9 mL, 0.14 mol, Spectrochem, India) was then added at room temperature, and the reaction mixture was stirred overnight. After completion of the reaction (monitored by TLC, 30% EtOAc in hexane), the reaction mixture was quenched with ice water, following which the solid product precipitated. The solid was collected by filtration and washed with n-hexane to give the title compound. 1H-NMR (400 MHz, DMSO-d6): δ 7.88 (d, J=8.4 Hz, 1H), 7.64 (d, J=8.8 Hz, 1H), 3.92 (s, 3H), 2.44 (s, 3H). MS (ESI, positive ion) m/z: 169 (M+H).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customthe reaction mixture was quenched with ice water
  3. customprecipitated
  4. filtrationThe solid was collected by filtration
  5. washwashed with n-hexane

Sources & evidence

ORD record
ord-7a2eaececb364ff2a5f9ab703baeee30
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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