Methanol → Methyl [(3,6-dichloro-2-methoxybenzoyl)aminooxy]acetate

HRID 568743Notes

Reaction equation

HRID 568743 reaction equation
[OH-].[K+].CO.[Cl:5][C:6]1[C:7]([O:17][CH3:18])=[C:8]([C:13]([Cl:16])=[CH:14][CH:15]=1)[C:9]([NH:11][OH:12])=[O:10].[CH3:19][O:20][C:21](=[O:24])[CH2:22]Br>C(Cl)Cl>[Cl:5][C:6]1[C:7]([O:17][CH3:18])=[C:8]([C:13]([Cl:16])=[CH:14][CH:15]=1)[C:9]([NH:11][O:12][CH2:22][C:21]([O:20][CH3:19])=[O:24])=[O:10]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 14797Potassium Hydroxide2×HCID 60984Methyl bromoacetateHCID 140973413,6-Dichloro-2-methoxybenzohydroxamic acid

Product 1

HCID 14097344Methyl [(3,6-dichloro-2-methoxybenzoyl)aminooxy]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.15 g. of potassium hydroxide in 50 ml. of methanol was added 7.55 g. of 3,6-dichloro-2-methoxy benzohydroxamic acid followed by stirring until dissolution was obtained. To this solution was added dropwise 3.03 ml. methylbromoacetate in 25 ml. of methanol. The reaction mixture was refluxed for 2 hours and allowed to stir overnight at ambient temperature. To the reaction mixture was added 0.36 g. of additional potassium hydroxide and the mixture heated to reflux for 4 hours, then cooled, filtered, and the filtrate concentrated in vacuo to give a crude semi-solid product. This crude product was taken up in methylene chloride and washed with water, 5% aqueous NaHCO3, brine, then dried over MgSO4, filtered and evaporated in vacuo to give a viscuous oil. The oil crystallized from an ethyl acetate-hexane mixture to the title product as a white solid, m.p. 102°-105° C.

Workup

  1. customwas obtained
  2. additionTo this solution was added dropwise 3.03 ml
  3. temperatureThe reaction mixture was refluxed for 2 hours
  4. stirringto stir overnight at ambient temperature
  5. additionTo the reaction mixture was added 0.36 g
  6. temperatureto reflux for 4 hours
  7. temperaturecooled
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo
  10. customto give a crude semi-solid product
  11. washwashed with water, 5% aqueous NaHCO3, brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. customevaporated in vacuo
  15. customto give a viscuous oil
  16. customThe oil crystallized from an ethyl acetate-hexane mixture to the title product as a white solid, m.p. 102°-105° C.

Sources & evidence

ORD record
ord-525efe4793734be1b88e99f70ee35462
Source dataset
uspto-grants-1988_03
Patent number
US04729781

Reaction notes

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