Methyl Anthranilate → HCID 20069137, compound

HRID 982039Notes

Reaction equation

HRID 982039 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([O:20][CH3:21])(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH2:14].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:1]1([CH2:7][CH2:8][CH2:9][NH:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[C:11]([O:20][CH3:21])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8635Methyl AnthranilateHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzene

Product 1

HCID 20069137HCID 20069137, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 14 g of 3-phenylpropyl bromide, 7.5 g of methyl anthranilate and 18 g of finely ground anhydrous potassium carbonate in 40 ml of anhydrous dioxane is boiled under a reflux condenser with a protective atmosphere of argon gas for about 60 hours, with magnetic stirring. After the solvent has been removed by distillation, 200 ml of methylene chloride and 100 ml of water are added, the organic phase is separated off and dried over magnesium sulfate, and the solvent is driven off. Column chromatography of the residue on silica gel (mobile phase toluene/methanol=10:1) provides methyl 2-(3-phenylpropylamino)benzoate as a viscous yellow oil.

Workup

  1. customAfter the solvent has been removed by distillation, 200 ml of methylene chloride and 100 ml of water
  2. additionare added
  3. customthe organic phase is separated off
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-f748f6a85f5e49edbb2a224b144d7418
Source dataset
uspto-grants-1991_02
Patent number
US04994493

Reaction notes

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