Methyl iodide → Methyl 2-chloro-5-nitroisonicotinate

HRID 77391Notes

Reaction equation

HRID 77391 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[C:14](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1)[C:5]([O:7][CH3:14])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 184406222-Chloro-5-nitroisonicotinic acid2×

Product 1

HCID 45480451Methyl 2-chloro-5-nitroisonicotinateYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-nitroisonicotinic acid (Intermediate 25A) (0.64 g, 3.17 mmol) in DMF (15 mL) under nitrogen was added sodium carbonate (1.0 g, 9.51 mmol). Reaction cooled in an ice bath and methyliodide (1.35 g, 9.51 mmol) was added dropwise. After complete addition, reaction allowed to warm to room temperature and stirred overnight under nitrogen. The reaction mixture was filtered and concentrated. The resultant crude material was purified by a 20 g silica column eluting with 40% ethylacetate in hexane to afford methyl 2-chloro-5-nitroisonicotinate (0.62 g, 2.86 mmol).

Workup

  1. customReaction
  2. temperaturecooled in an ice bath
  3. additionAfter complete addition, reaction
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated
  6. customThe resultant crude material was purified by a 20 g silica column
  7. washeluting with 40% ethylacetate in hexane

Sources & evidence

ORD record
ord-780c14261612436a84ead8ce4bed271c
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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