Hydroxyamine hydrochloride → (NE)-N-(5-ethenyl-2,3-dihydroinden-1-ylidene)hydroxylamine

HRID 1506494ノート

反応式

HRID 1506494 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2)=[CH2:2].Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>CO>[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)/[C:8](=[N:14]/[OH:15])/[CH2:7][CH2:6]2)=[CH2:2]

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 671719145-vinyl-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 87295219(NE)-N-(5-ethenyl-2,3-dihydroinden-1-ylidene)hydroxylamine収率 98.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 5-vinyl-2,3-dihydro-1H-inden-1-one (Preparation 87A, 1.05 g, 6.64 mmol), hydroxylamine hydrochloride (0.553 g, 7.96 mmol) and methanol (20 mL) at room temperature was added sodium acetate (0.653 g, 7.96 mmol). The reaction mixture was stirred at 60° C. for 1 hr and at room temperature overnight. The heterogeneous mixture was concentrated and water (20 mL) was added. The mixture was heated to ˜60° C. and then cooled. The solid was filtered, washed with a mixture of water and ethanol (1:1) and dried to give (E)-5-vinyl-2,3-dihydro-1H-inden-1-one oxime (1.13 g, 6.52 mmol, 98% yield) as a yellow solid. The product had an HPLC ret. time=2.72 min. (condition C); LC/MS M+1=174.3.

後処理

  1. concentrationThe heterogeneous mixture was concentrated
  2. additionwater (20 mL) was added
  3. temperatureThe mixture was heated to ˜60° C.
  4. temperaturecooled
  5. filtrationThe solid was filtered
  6. washwashed with a mixture of water and ethanol (1:1)
  7. customdried

出典と根拠

ORDレコード
ord-f1f2da92fcdc417f899b54e66246744d
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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