Ethanol → 2,6-Dichloro-3-nitrobenzylideneaminooxyacetic Acid

HRID 905367Notes

Reaction equation

HRID 905367 reaction equation
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:3]=1[CH:4]=O.C(O)C.[ClH:17].[C:18]([CH2:21][O:22][NH2:23])([OH:20])=[O:19].C(CON)(O)=O.C([O-])(=O)C.[Na+]>O>[Cl:17][CH:21]([O:22][N:23]=[CH:4][C:3]1[C:6]([Cl:13])=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[CH:2]=1)[C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 2723609Aminooxyacetic acid hemihydrochlorideHCID 27949122,6-Dichloro-3-nitrobenzaldehyde

Product 1

HCID 1317133262,6-Dichloro-3-nitrobenzylideneaminooxyacetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A warm solution of 2,6-dichloro-3-nitrobenzaldehyde, 1.8 gm. in 20 ml. of ethanol was stirred into a solution of 0.9 gm. (0.008 equivs.) of carboxymethoxylamine hemihydrochloride and 0.45 gm. of sodium acetate, anhyd., in 20 ml. of water at room temperature. The mixture was heated on the steam bath for one-half hour, and was then evaporated to dryness at room temperature. The residue was triturated with cold water, filtered, washed with cold water and dried in air to obtain 2.1 gm. (87.4%) of crude material melting at 76°-84° C. This was purified from aqueous-methanol to obtain 1.9 gm. of pale cream-colored product melting at 82°-85° C.

Workup

  1. customat room temperature
  2. temperatureThe mixture was heated on the steam bath for one-half hour
  3. customwas then evaporated to dryness at room temperature
  4. customThe residue was triturated with cold water
  5. filtrationfiltered
  6. washwashed with cold water
  7. customdried in air
  8. customto obtain 2.1 gm
  9. customThis was purified from aqueous-methanol
  10. customto obtain 1.9 gm

Sources & evidence

ORD record
ord-53d2f437ebe943f9bff6bf863ea181a4
Source dataset
uspto-grants-1983_12
Patent number
US04423241

Reaction notes

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