Methyl Anthranilate → HCID 15922435, compound

HRID 2304754Notes

Reaction equation

HRID 2304754 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1.[NH2:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]>C(C(C)=O)C>[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8635Methyl AnthranilateHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromide

Product 1

HCID 15922435HCID 15922435, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 77 g of potassium carbonate in a mixture of 100 mL of methyl ethyl ketone, 50 g of 4-fluorobenzyl bromide and 26 mL of the methyl 2-aminobenzoate was refluxed for 8 h, cooled to room temperature, filtered and concentrated. Filtration on 600 mL of silica gel and washing with 10% ethyl acetate in hexane afforded the desired material as a yellow oil (41 g, 85% purity). This material was used as such for the next step.

Workup

  1. temperaturewas refluxed for 8 h
  2. filtrationfiltered
  3. concentrationconcentrated
  4. filtrationFiltration on 600 mL of silica gel
  5. washwashing with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d317d78e27d84721a9d6e17d921a35ca
Source dataset
uspto-grants-2002_08
Patent number
US06436965B1

Reaction notes

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