Methyl iodide → HCID 67042273, compound

HRID 1929285Notes

Reaction equation

HRID 1929285 reaction equation
[NH2:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].[CH3:19]I>CN(C=O)C>[Cl:13][C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([N+:14]([O-:16])=[O:15])[C:2]=1[NH:1][CH3:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67042319HCID 67042319, compound

Product 1

HCID 67042273HCID 67042273, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.18 g (13.0 mmol) of ethyl 3-amino-4-chloro-2-nitrobenzoate were introduced in DMF and admixed under a nitrogen atmosphere with 0.624 g (15.6 mmol) of sodium hydride. The mixture was left with stirring for 30 minutes and then 2.21 g (15.6 mmol) of methyl iodide were added. After a further 2.5 h of stirring at room temperature the mixture was concentrated and the residue was extracted with ethyl acetate, washed with water, and then dried over MgSO4. The product was then subjected to chromatographic separation (silica gel, heptane/ethyl acetate 9:1).

Workup

  1. waitThe mixture was left
  2. stirringAfter a further 2.5 h of stirring at room temperature the mixture
  3. concentrationwas concentrated
  4. extractionthe residue was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customThe product was then subjected to chromatographic separation (silica gel, heptane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-ac37bf8d6b5b459bae86411be3655b84
Source dataset
uspto-grants-2012_05
Patent number
US08188002B2

Reaction notes

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