Hydroxylamine → HCID 86600606, compound

HRID 1988104Notes

Reaction equation

HRID 1988104 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]2[C:19]#[N:20])=[O:7])=[CH:4][CH:3]=1.[NH2:23][OH:24]>CO>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]2[C:19](=[N:23][OH:24])[NH2:20])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 11381296HCID 11381296, compound

Product 1

HCID 86600606HCID 86600606, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1-(4-chlorobenzoyl)-6-methyl-1,2-dihydroquinoline-2-carbonitrile (200 mg) in methanol (1 mL) was added cold 1M hydroxylamine in methanol (971 μL). The reaction mixture was warmed to ambient conditions and stirred overnight. The methanol is removed in vacuo and the crude product is purified by liquid chromatography (gradient elution of acetonitrile (0.02% trifluoroacetic acid)/water (0.02% trifluoroacetic acid) through a reverse phase C18 column) to give the titled compound (25 mg, 11% yield) as a pale yellow solid. (M+H)+−342.

Workup

  1. temperatureThe reaction mixture was warmed to ambient conditions
  2. customThe methanol is removed in vacuo
  3. customthe crude product is purified by liquid chromatography (
  4. washgradient elution of acetonitrile (0.02% trifluoroacetic acid)/water (0.02% trifluoroacetic acid) through a reverse phase C18 column)

Sources & evidence

ORD record
ord-8b306e68be6a488a81eedab10b52fe82
Source dataset
uspto-grants-2009_06
Patent number
US07553967B2

Reaction notes

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