Hydrochloric Acid → 2,5-Dimethoxy-N-methylcinnamohydroxamic acid

HRID 620403Notes

Reaction equation

HRID 620403 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:4]=1[CH:5]=[CH:6][C:7](O)=[O:8].C(Cl)(=O)C(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH3:29][NH:30][OH:31].Cl>CN(C)C=O.ClCCl.CC(C)=O.C(OCC)(=O)C.CCCCCC.O>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:4]=1[CH:5]=[CH:6][C:7]([N:30]([CH3:29])[OH:31])=[O:8]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 77906N-methylhydroxylamine hydrochlorideHCID 1145783-(2,5-Dimethoxyphenyl)-2-propenoic acid

Product 1

HCID 543050542,5-Dimethoxy-N-methylcinnamohydroxamic acidYield 40.5%

Reagents, catalysts & solvents 5

HCID 6228DimethylformamideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 2,5-dimethoxycinnamic acid (2.08 g, 10 mmol), oxalyl chloride (0.96 ml, 11 mmol) and N,N-dimethylformamide (two drops) in 25 ml dichloromethane was stirred for 20 minutes. The resulting solution was evaporated to leave a yellow solid, which was then dissolved in 10 ml of acetone. This solution was added slowly to a stirred mixture of water (20 ml), sodium carbonate (2.5 g, 24 mmol), and N-methylhydroxylamine hydrochloride (1.06 g, 12.7 mmol), cooled to 5° C. The resulting mixture was stirred for 20 minutes, then poured into excess 1M hydrochloric acid and extracted twice with ethyl acetate. The extracts were washed wth water and 1N NaHCO3, dried over MgSO4, and evaporated to leave an orange oil. Chromatography on silica gel with 7:3 ethyl acetate-hexane provided 0.96 g (40% yield) of the named compound, mp 111°-112° C., after recrystallization from hexane-1,2-dichloroethane.

Workup

  1. customThe resulting solution was evaporated
  2. customto leave a yellow solid, which
  3. extractionextracted twice with ethyl acetate
  4. washThe extracts were washed wth water and 1N NaHCO3
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto leave an orange oil

Sources & evidence

ORD record
ord-c420feb90c5e462eb4f3a720d1e7b492
Source dataset
uspto-grants-1989_04
Patent number
US04820828

Reaction notes

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