Allyl bromide → HCID 14883224, compound

HRID 2074005Notes

Reaction equation

HRID 2074005 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:13])[C:5](=[CH:10][C:11]=1[Cl:12])[C:6]([O:8][CH3:9])=[O:7].[CH2:14](Br)[CH:15]=[CH2:16].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:16]([O:13][C:4]1[CH:3]=[C:2]([NH2:1])[C:11]([Cl:12])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14883223Methyl 4-amino-5-chloro-2-hydroxybenzoate

Product 1

HCID 14883224HCID 14883224, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 4-amino-5-chlorosalicylate (5 g), allyl bromide (12.6 g), ground K2CO3 (30 g) and acetone (120 ml) is stirred at reflux for 5 hours and cooled to 25° C. The mixture is partitioned between methylene chloride and H2O, the organic layer is separated, dried (MgSO4), filtered and evaporated. The residue is recrystallized from hexanechloroform affording the desired product as a crystalline solid (M.P. 107°-109° C.).

Workup

  1. temperatureat reflux for 5 hours
  2. customThe mixture is partitioned between methylene chloride and H2O
  3. customthe organic layer is separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is recrystallized from hexanechloroform

Sources & evidence

ORD record
ord-8f61c748080244508856580fd740e409
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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