2-Chloro-6-nitrobenzaldehyde → 2-Chloro-6-nitrobenzylideneaminooxyacetic Acid

HRID 905369Notes

Reaction equation

HRID 905369 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=O.[ClH:13].[C:14]([CH2:17][O:18][NH2:19])([OH:16])=[O:15].C(CON)(O)=O.C([O-])(=O)C.[Na+]>O>[Cl:13][CH:17]([O:18][N:19]=[CH:4][C:3]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][CH:2]=1)[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 807012-Chloro-6-nitrobenzaldehydeHCID 517045Sodium AcetateHCID 2723609Aminooxyacetic acid hemihydrochloride

Product 1

HCID 1317133282-Chloro-6-nitrobenzylideneaminooxyacetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A warm solution of 2.5 gm. (0.014 mole) of 2-chloro-6-nitrobenzaldehyde in 40 ml. of alcohol 3A was added, with stirring, to a warm solution of 1.5 gm. (0.014 equivs.) of carboxymethoxylamine hemihydrochloride and 1.7 gm. (0.021 equiv.) of anhyd. sodium acetate in 40 ml. of water. The reaction mixture was heated a half-hour on the steam bath, and was then evaporated to a volume of about 20 ml. A solid separated upon cooling; it was filtered from the mixture, washed with cold water and dried in air to give 2.7 gm. (77.3%) of tan-yellow colored material melting at 136°-141° C. Recrystallization from n-hexane/isopropyl alcohol yield 2.5 gm. of pale tan-yellow crystalline product melting at 144°-146° C.

Workup

  1. temperatureThe reaction mixture was heated a half-hour on the steam bath
  2. customwas then evaporated to a volume of about 20 ml
  3. customA solid separated
  4. temperatureupon cooling
  5. filtrationit was filtered from the mixture
  6. washwashed with cold water
  7. customdried in air
  8. customto give 2.7 gm
  9. customRecrystallization from n-hexane/isopropyl alcohol yield 2.5 gm

Sources & evidence

ORD record
ord-251cd786746845e297bdf387c5c86065
Source dataset
uspto-grants-1983_12
Patent number
US04423241

Reaction notes

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