Hexane → 2-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)-N-hydroxy-N-methylpropanamide

HRID 357250Notes

Reaction equation

HRID 357250 reaction equation
Cl.[CH3:2][NH:3][OH:4].[O:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([CH:21]([CH3:25])[C:22](Cl)=[O:23])=[CH:20][C:7]1=2.CCCCCC>N1C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[O:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([CH:21]([CH3:25])[C:22]([N:3]([OH:4])[CH3:2])=[O:23])=[CH:20][C:7]1=2

Participants

7

Reactant 3

HCID 8058HexaneHCID 77906N-methylhydroxylamine hydrochlorideHCID 867533582-(6,11-Dihydro11oxodibenz[b,e]oxepin-2-yl)propionyl chloride

Product 1

HCID 105190732-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)-N-hydroxy-N-methylpropanamideYield 65.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 16.6 g of N-methylhydroxylamine hydrochloride in 400 ml of dry pyridine was chilled and treated dropwise over several minutes with a solution of 15.7 g of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl) propionyl chloride in 500 ml of tetrahydrofuran. The solution was allowed to equilibrate to room temperature with continued stirring. Thin layer analysis (silica gel, 30% hexane in ethyl acetate) indicated reaction completion after 5 hours. Pyridine and tetrahydrofuran were removed in vacuo and the resulting mixture was partitioned against a total of 700 ml of methylene chloride and 2000 ml of 10% HCl (pH of aqueous layers <1). The organic phase was washed with 500 ml of water. The dried (Na2 SO4) organic phase was concentrated in vacuo to an oil. Thin layer analysis indicated a mixture, which was separated via preparative HPLC to give 10.58 g of the product, 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)-N-hydroxy-N-methylpropanamide, as an oil.

Workup

  1. customto equilibrate to room temperature with continued stirring
  2. customreaction completion after 5 hours
  3. customPyridine and tetrahydrofuran were removed in vacuo
  4. customthe resulting mixture was partitioned against a total of 700 ml of methylene chloride and 2000 ml of 10% HCl (pH of aqueous layers <1)
  5. washThe organic phase was washed with 500 ml of water
  6. customThe dried (Na2 SO4) organic phase
  7. concentrationwas concentrated in vacuo to an oil
  8. customwas separated via preparative HPLC

Sources & evidence

ORD record
ord-e80a501078824b1e8748eae564445fca
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Reaction notes

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