Hydroxyamine hydrochloride → 1-[3-(Chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone oxime

HRID 1791056Notes

Reaction equation

HRID 1791056 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].Cl.[NH2:7][OH:8].[Cl:9][CH:10]=[C:11]1[CH:17]=[CH:16][C:15]2[CH:18]=[C:19]([CH:22]=O)[CH:20]=[CH:21]C=2O[CH2:12]1>CO>[Cl:9][CH:10]=[C:11]1[CH:17]=[CH:16][C:15]2[CH:18]=[C:19]([C:20](=[N:7][OH:8])[CH3:21])[CH:22]=[CH:2][C:1]=2[O:4][CH2:12]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 74027557HCID 74027557, compound

Product 1

HCID 865953681-[3-(Chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone oximeYield 103.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12.3 mg (0.15 mmol) of sodium acetate and then 10.4 mg (0.15 mmol) of hydroxylamine hydrochloride are added at ambient temperature to 30 mg (0.136 mmol) of 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carbaldehyde, prepared according to example 72, in solution in 2 ml of methanol. The solution is stirred for 24 hours and is then hydrolyzed. A conventional treatment makes it possible to obtain 35 mg (100%) of 1-[3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone oxime in the solid form; 1H NMR: 7.9–8.3 (broad s, OH), 8.10 (8.05) (s, 1H), 7.35–7.45 (m, 2H), 7.03 (7.00) (d, J=8.4 Hz, 1H), 6.84 (d, J=11.7 Hz, 1H), 6.35 (s, 3H), 4.88 (4.57)(s, 2H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-68307f44708f49ae8a56e3c5e7660de9
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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