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

HRID 1506494노트

반응식

HRID 1506494 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f1f2da92fcdc417f899b54e66246744d
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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