Hydroxyamine hydrochloride → 5,6,7,8,9,10-Hexahydro-6,9-methanobenzo[a][8]annulen-11-one oxime

HRID 1394406Notes

Reaction equation

HRID 1394406 reaction equation
[CH:1]1[C:6]2[CH2:7][CH:8]3[C:13](=O)[CH:11]([CH2:12][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH2:10][CH2:9]3.Cl.[NH2:16][OH:17]>N1C=CC=CC=1.CCO>[CH:1]1[C:6]2[CH2:7][CH:8]3[C:13](=[N:16][OH:17])[CH:11]([CH2:12][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH2:10][CH2:9]3

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 5260406Tricyclo[8.2.1.03,8]trideca-3,5,7-trien-13-one

Product 1

HCID 130264515,6,7,8,9,10-Hexahydro-6,9-methanobenzo[a][8]annulen-11-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

To a solution of 34.3 g of 5,6,7,8,9,10-hexahydro-6,9-methano-benzo[a][8]annulen-11-one (0.184 mol) in 100 mL of pyridine and 100 mL of EtOH was added 29.7 g of hydroxylamine hydrochloride (0.460 mol). The resultant solution was refluxed for 4 hours prior to concentration in vacuo. The residue was partitioned between CH2Cl2 and 10% aqueous citric acid. The aqueous layer was extracted with CH2Cl2 (4×200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the oxime.

Workup

  1. concentrationto concentration in vacuo
  2. customThe residue was partitioned between CH2Cl2 and 10% aqueous citric acid
  3. extractionThe aqueous layer was extracted with CH2Cl2 (4×200 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca59e8d6060a4448b93986ddc2b11285
Source dataset
uspto-grants-2008_03
Patent number
US07348431B2

Reaction notes

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