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

HRID 1527965ノート

反応式

HRID 1527965 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-44f132621c5d4f3aa35c7926039df91b
出典データセット
uspto-grants-2015_07
特許番号
US09090565B2

反応ノート

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