Pyridine → HCID 73607868, compound

HRID 1735854Notes

Reaction equation

HRID 1735854 reaction equation
[CH2:1]([C:4]1([CH2:19][CH:20]=O)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].Cl.[NH2:23][OH:24].N1C=CC=CC=1>ClCCl>[CH2:1]([C:4]1([CH2:19][CH:20]=[N:23][OH:24])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 19079062HCID 19079062, compound

Product 1

HCID 73607868HCID 73607868, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved 2-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-ethanal (1.00 g, 3.62 mmol) in 10 mL of dry dichloromethane under a nitrogen atmosphere. Added 3A sieves, hydroxylamine hydrochloride (0.38 g, 5.43 mmol), and pyridine (0.58 mL, 0.57 g, 7.24 mmol). Stirred at room temperature for 16 hours. Filtered to remove sieve dust, and washed solid with water and dichloromethane. Separated layers of filtrate. Dried organic solution with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 20% EtOAc-CH2Cl2. Combined appropriate fractions and evaporated to give 0.65 g (62% yield) of 2-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-ethanone oxime as a colorless oil.

Workup

  1. filtrationFiltered
  2. customto remove sieve dust
  3. washwashed solid with water and dichloromethane
  4. filtrationDried organic solution with MgSO4, filtered
  5. customevaporated
  6. customPurified crude product by flash chromatography on silica gel eluting with 20% EtOAc-CH2Cl2
  7. customevaporated

Sources & evidence

ORD record
ord-dc236b9428f54078a4a9664a8ff4a470
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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