1-(2-Hydroxy-3-methylphenyl)ethan-1-one → 6-[1-(Hydroxyamino)ethylidene]-2-methylcyclohexa-2,4-dien-1-one

HRID 873880ノート

反応式

HRID 873880 の反応式
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=O)[CH3:10].CC([O-])=O.[Na+].Cl.[NH2:18][OH:19]>CO.[Cl-].[Na+].O>[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1/[C:9](=[N:18]/[OH:19])/[CH3:10]

参加物

6

反応物 3

HCID 2404371-(2-Hydroxy-3-methylphenyl)ethan-1-oneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 1370147826-[1-(Hydroxyamino)ethylidene]-2-methylcyclohexa-2,4-dien-1-one収率 89.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
60 °C

実験手順

1-(2-hydroxy-3-methylphenyl)ethanone (Step 46.1) (900 mg, 5.87 mmol) was dissolved in MeOH (15 mL) and NaOAc (771 mg, 9.40 mmol) and hydroxylamine hydrochloride (612 mg, 8.81 mmol) were successively added. The resulting mixture was heated up and stirred at 60° C. for 2 hr. The reaction mixture was poured into brine and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product (964 mg, 5.25 mmol, 89% yield) as a colorless solid. tR: 0.94 min (LC-MS 2); ESI-MS: 166 [M+H]+, ESI-MS: 164 [M−H]− (LC-MS 2); Rf=0.66 (hexane/EtOAc 1:1).

後処理

  1. temperatureThe resulting mixture was heated up
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-2697d2e75fe9400cb9dd7ebee98790f2
出典データセット
uspto-grants-2015_03
特許番号
US08975417B2

反応ノート

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