Hydroxyamine hydrochloride → Methyl 7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate

HRID 1506390노트

반응식

HRID 1506390 반응식
O=[C:2]([CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:17]=[CH2:18])[CH:13]=2)[C:8]1=[O:19])[C:3]([O:5][CH3:6])=[O:4].Cl.[NH2:21]O>CO>[CH:17]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[C:8]1[O:19][N:21]=[C:2]([C:3]([O:5][CH3:6])=[O:4])[C:7]=1[CH2:16][CH2:15]2)=[CH2:18]

참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 67171899Methyl 2-oxo-2-(1-oxo-6-vinyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetate

생성물 1

HCID 68182163Methyl 7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate수율 35.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of methyl 2-oxo-2-(1-oxo-6-vinyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetate (Preparation 45A, 180 mg, 0.697 mmol) and hydroxylamine hydrochloride (145 mg, 2.091 mmol) in methanol (3 mL) was stirred at reflux for 60 min. The reaction mixture was allowed to stir at room temperature overnight. The product crystallized from solution upon stirring at room temperature. The solid was collected by vacuum filtration and dried to give methyl 7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate (65 mg, 0.244 mmol, 35.1% yield over two steps) as yellow solid. The compound had an HPLC ret. time=1.05/2.0 min. (condition E); MS:(M+H)=256.2.

후처리

  1. temperatureat reflux for 60 min
  2. stirringto stir at room temperature overnight
  3. customThe product crystallized from solution
  4. stirringupon stirring at room temperature
  5. filtrationThe solid was collected by vacuum filtration
  6. customdried

출처 및 근거

ORD 기록
ord-cc4908b471544aee8bc120bfd8edfa8b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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