Salicylhydroxamic Acid → HCID 12365946, compound

HRID 2398046Notes

Reaction equation

HRID 2398046 reaction equation
[C:1]([NH:10][OH:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(O[CH:15](OCC)[CH2:16][CH2:17][CH2:18]Cl)C>C(O)(=O)C>[O:11]1[N:10]2[CH:18]([O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1]2=[O:9])[CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 66644Salicylhydroxamic AcidHCID 2625984-Chlorobutyraldehyde Diethyl Acetal

Product 1

HCID 12365946HCID 12365946, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Salicylhydroxamic acid (30 g.) and 36 g. of 4-chlorobutyraldehyde diethyl acetal were allowed to react in acetic acid as described in Example 1. The reaction mixture was transferred to an ice-water mixture, stirred well, and decanted to remove the aqueous layer. The oil was washed again with water and allowed to stand at room temperature whereupon crystallization occurred. Aqueous solution of ammonium hydroxide was added, mixture was warmed and stirred and then allowed to stand overnight at room temperature. The aqueous solution was decanted from the partially crystallized oil and the latter was triturated with ethanol yielding 9.5 g. of solid melting at 137.5°-139.5° C. After recrystallization from methanol, the product (7 g.) melted at 139°-141° C.

Workup

  1. customdecanted
  2. customto remove the aqueous layer
  3. washThe oil was washed again with water
  4. customto stand at room temperature whereupon crystallization
  5. additionAqueous solution of ammonium hydroxide was added
  6. temperaturemixture was warmed
  7. stirringstirred
  8. customThe aqueous solution was decanted from the partially crystallized oil
  9. customthe latter was triturated with ethanol yielding 9.5 g
  10. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-d0052cc614c64f2db5c0e3b5b67da4e3
Source dataset
uspto-grants-1977_05
Patent number
US04024139

Reaction notes

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