Hydroxyamine hydrochloride → (NE)-N-[(3R)-3-(4-bromophenyl)-3-(2-methylphenyl)-1-pyridazin-4-ylpropylidene]hydroxylamine

HRID 1527965Notes

Reaction equation

HRID 1527965 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[N:14][CH:13]=2)=O)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].Cl.[NH2:31][OH:32]>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[CH2:9]/[C:10](/[C:12]2[CH:17]=[CH:16][N:15]=[N:14][CH:13]=2)=[N:31]\[OH:32])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 86684791(R)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one

Product 1

HCID 136249444(NE)-N-[(3R)-3-(4-bromophenyl)-3-(2-methylphenyl)-1-pyridazin-4-ylpropylidene]hydroxylamineYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial was added (R)-3-(4-bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one (30 trig, 79 μmol), sodium hydrogencarbonate (20 mg, 0.24 mmol) and hydroxylamine hydrochloride (16 mg, 0.24 mmol) in ethanol (1 mL) and water (0.02 mL). The vial was capped and heated at 120° C. for 10 min, then the reaction mixture was partitioned between ethyl acetate and poured onto water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; gradient dichloromethane to dichloromethane/methanol/25% aq. anmmonia solution 95:5:0.25) afforded the title compound (28 mg, 90%). White foam, MS: 396.1 [M+H]+.

Workup

  1. customThe vial was capped
  2. customthe reaction mixture was partitioned between ethyl acetate
  3. additionpoured onto water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-44f132621c5d4f3aa35c7926039df91b
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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