N-Ethylhydroxylamine hydrochloride → 2-(6,11-dihydro-11-oxodibenz[b,e]-oxepin-2-yl)-N-ethyl-N-hydroxypropanamide

HRID 357251Notes

Reaction equation

HRID 357251 reaction equation
Cl.[CH2:2]([NH:4][OH:5])[CH3:3].[O:6]=[C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][O:10][C:9]2[CH:18]=[CH:19][C:20]([CH:22]([CH3:26])[C:23](Cl)=[O:24])=[CH:21][C:8]1=2>N1C=CC=CC=1.O1CCCC1>[O:6]=[C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][O:10][C:9]2[CH:18]=[CH:19][C:20]([CH:22]([CH3:26])[C:23]([N:4]([CH2:2][CH3:3])[OH:5])=[O:24])=[CH:21][C:8]1=2

Participants

5

Reactant 2

HCID 10219386N-Ethylhydroxylamine hydrochlorideHCID 867533582-(6,11-Dihydro11oxodibenz[b,e]oxepin-2-yl)propionyl chloride

Product 1

HCID 105200852-(6,11-dihydro-11-oxodibenz[b,e]-oxepin-2-yl)-N-ethyl-N-hydroxypropanamideYield 30.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirring solution of 10.14 g of N-ethylhydroxylamine hydrochloride in 350 ml of dry pyridine was chilled and treated dropwise over several minutes with a solution of 8.0 g of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)propionyl chloride in 400 ml of tetrahydrofuran. The solution was allowed to equilibrate to room temperature overnight (16 hours) with continued stirring. The reaction was quenched with 500 ml of water and concentrated in vacuo to remove solvents. The product mixture was partitioned against a total of 500 ml of methylene chloride and 1000 ml of 10% HCl (pH of aqueous layers <1). The organic phase was washed with 500 ml of water, dried (Na2SO4) and concentrated in vacuo to an oil. Thin layer analysis indicated a mixture, which was separated twice via preparative HPLC to give 2.65 g of 2-(6,11-dihydro-11-oxodibenz[b,e]-oxepin-2-yl)-N-ethyl-N-hydroxypropanamide, as an oil.

Workup

  1. custom(16 hours)
  2. customThe reaction was quenched with 500 ml of water
  3. concentrationconcentrated in vacuo
  4. customto remove solvents
  5. customThe product mixture was partitioned against a total of 500 ml of methylene chloride and 1000 ml of 10% HCl (pH of aqueous layers <1)
  6. washThe organic phase was washed with 500 ml of water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo to an oil
  9. customwas separated twice via preparative HPLC

Sources & evidence

ORD record
ord-1a395e41993548a68fe17a5494b891b0
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Reaction notes

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