Anthranilic Acid → HCID 21832987, compound

HRID 1740768Notes

Reaction equation

HRID 1740768 reaction equation
C(N(CC)CC)C.[C:8]([OH:17])(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].[Cl:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=O.C(Cl)(=O)OCC>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:18][CH2:19][CH2:20][CH2:21][C:22]1[O:16][C:8](=[O:17])[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 783704-Chlorobutyryl chloride

Product 1

HCID 21832987HCID 21832987, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (7.60 ml) was added to a suspension of anthranilic acid (3.52 g) in methylene chloride (35 ml) and then the mixture was cooled with ice. The mixture, with 4-chlorobutyryl chloride (3.62 g) dropwise added thereto, was stirred for 3 hours at room temperature and then cooled with ice. The reaction mixture, with triethylamine (4.00 ml) and ethyl chlorocarbonate (2.70 ml) dropwise added thereto, was stirred for 1 hour at 0° C. and further for 3 hours at room temperature. The reaction mixture, with chloroform added thereto, was washed with water and saturated brine successively. The organic layer was dried over sodium sulfate anhydride and then concentrated. The residue was purified by silica gel column chromatography (silica gel 125 g, chloroform-hexane), thereby yielding 4.00 g of the aimed compound as yellow solid.

Workup

  1. temperaturethe mixture was cooled with ice
  2. temperaturecooled with ice
  3. stirringwas stirred for 1 hour at 0° C. and further for 3 hours at room temperature
  4. washwas washed with water and saturated brine successively
  5. dry with materialThe organic layer was dried over sodium sulfate anhydride
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (silica gel 125 g, chloroform-hexane)

Sources & evidence

ORD record
ord-15d79e082da34329b41b05a2629fbac0
Source dataset
uspto-grants-1999_10
Patent number
US05972929

Reaction notes

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