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

HRID 1527965노트

반응식

HRID 1527965 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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온도
120 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-44f132621c5d4f3aa35c7926039df91b
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090565B2

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