Hydrochloric Acid → HCID 86735113, compound

HRID 2072519Notes

Reaction equation

HRID 2072519 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:16])[CH:14]=O)=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2.Cl.[NH2:22][OH:23].[OH-].[Na+].Cl>O.C(O)C>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:16])[CH:14]=[N:22][OH:23])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 214093832-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal

Product 1

HCID 86735113HCID 86735113, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.288 g. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal in 4 ml. of ethanol is added a solution of 0.12 g. of hydroxylamine hydrochloride and 0.11 g. of sodium hydroxide in 0.4 ml. of water. The mixture is refluxed briefly, then acidified with dilute hydrochloric acid and extracted with ethyl acetate. The extract is washed, dried and evaporated to yield a crude product which is chromatographed on silica gel, eluting with chloroform:methanol (19:1) to afford 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal oxime.

Workup

  1. temperatureThe mixture is refluxed briefly
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed
  4. customdried
  5. customevaporated
  6. customto yield a crude product which
  7. customis chromatographed on silica gel
  8. washeluting with chloroform:methanol (19:1)

Sources & evidence

ORD record
ord-9940313b5bd84752ba23d78d396ad60d
Source dataset
uspto-grants-1977_09
Patent number
US04051260

Reaction notes

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