Potassium Carbonate → 3-(2-hydroxyiminopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

HRID 26422Notes

Reaction equation

HRID 26422 reaction equation
[CH2:1]([C:5]1[C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:2]([CH3:4])=O.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:28][OH:29]>O.CO>[OH:29][N:28]=[C:2]([CH3:4])[CH2:1][C:5]1[C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 203329343-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Product 1

HCID 867364703-(2-hydroxyiminopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The starting material is prepared as follows: The mixture of 7.0 g of 3-acetonyl-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, 3.88 g of potassium carbonate, 3.55 g of hydroxylamine hydrochloride, 5 ml of water and 60 ml of methanol is refluxed for 5 hours and then stirred at room temperature overnight. 80 ml of water are added, the precipitate collected and washed with ethanol and diethyl ether, to yield the 3-(2-hydroxyiminopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone, melting at 155°-158°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for 5 hours
  3. customthe precipitate collected
  4. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-37f8067c2e314bbb8465a34fc1c3a49b
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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