Methyl iodide → HCID 63090729, compound

HRID 2274015Notes

Reaction equation

HRID 2274015 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5200412Methyl 5-Amino-2-chlorobenzoate

Product 1

HCID 63090729HCID 63090729, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

55.0 g (296 mmol) of methyl 2-chloro-5-aminobenzoate and 49.1 g (356 mmol) of potassium carbonate are suspended in 500 ml of acetonitrile p.a. 22.1 ml (356 mmol) of methyl iodide are added dropwise to the reaction mixture. The suspension is then boiled under reflux for 3 hours. After cooling, the reaction mixture is filtered. The filtrate is diluted with water. The aqueous phase is extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulphate and filtered. The solvent is removed under reduced pressure on a rotary evaporator. The crude product is purified by column chromatography. This gives 30.0 g (51%) of methyl 2-chloro-5-(methylamino)benzoate.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. additionThe filtrate is diluted with water
  5. extractionThe aqueous phase is extracted twice with ethyl acetate
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. filtrationfiltered
  8. customThe solvent is removed under reduced pressure on a rotary evaporator
  9. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-8b34931536e04ad6bdd0a9112e83db11
Source dataset
uspto-grants-2015_09
Patent number
US09126945B2

Reaction notes

Loading…