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

HRID 1506390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506390
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 68182163Methyl 7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylateAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cc4908b471544aee8bc120bfd8edfa8b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216972B2

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