Methyl iodide → Methyl 3-allyl-2-methoxy-4-amino-5-chlorobenzoate

HRID 2074006Notes

Reaction equation

HRID 2074006 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH2:9]([C:12]1[C:13]([OH:24])=[C:14]([CH:19]=[C:20]([Cl:23])[C:21]=1[NH2:22])[C:15]([O:17][CH3:18])=[O:16])[CH:10]=[CH2:11]>CC(C)=O>[CH2:9]([C:12]1[C:13]([O:24][CH3:1])=[C:14]([CH:19]=[C:20]([Cl:23])[C:21]=1[NH2:22])[C:15]([O:17][CH3:18])=[O:16])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14883228Methyl 3-allyl-2-hydroxy-4-amino-5-chlorobenzoate

Product 1

HCID 14883229Methyl 3-allyl-2-methoxy-4-amino-5-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of potassium carbonate (19 g), methyl iodide (8 g) and the phenolic compound of step 2 above (3.4 g) in acetone (100 ml) is stirred under reflux for about 6.4 hours. The mixture is partitioned between CH2Cl2 and H2O, and the organic layer is separated and washed with 10% aqueous HCl, dried (MgSO4) and evaporated affording an oil which chromatographed on silica gel affording the desired product which is used in the next step.

Workup

  1. temperatureunder reflux for about 6.4 hours
  2. customThe mixture is partitioned between CH2Cl2 and H2O
  3. customthe organic layer is separated
  4. washwashed with 10% aqueous HCl
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customaffording an oil which
  8. customchromatographed on silica gel affording the desired product which

Sources & evidence

ORD record
ord-b97d88257fa240919c5e7823ce7d5bc0
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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