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

HRID 1506390Notes

Reaction equation

HRID 1506390 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cc4908b471544aee8bc120bfd8edfa8b
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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