ChemicalBook CAS DataBase List Methyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)acetate

Methyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)acetate synthesis

7synthesis methods

Product Name:Methyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)acetate
CAS Number:866038-49-5
Molecular formula:C11H11NO4
Molecular Weight:221.21

methyl 2-(3-amino-4-hydroxyphenyl)acetate

78587-72-1
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$44.00/250mg

79-04-9 Synthesis

79-04-9
352 suppliers
$12.00/5g

Methyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)acetate

866038-49-5
19 suppliers
$365.00/500mg

Yield:866038-49-5 90%

Reaction Conditions:

with Sodium hydrogenocarbonate in lithium hydroxide monohydrate;ethyl acetate at 25; for 1 h;

Steps:

1.1 Stage 1: Methyl 2-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)acetate

Chloroacetyl chloride (1 equiv.) was added at room temperature to a mixture of methyl (3-amino-4-hydroxyphenyl)acetate (5.5 mmol) and sodium hydrogen carbonate (1.1 equiv.) in ethyl acetate (5 ml)/water (5 ml). The reaction mixture was stirred for 1 h, then the phases were separated and the organic phase was washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The crude product was dissolved in DMF (11 ml); activated potassium carbonate was added, and the mixture was stirred overnight at room temperature. The reaction mixture was then diluted with water and extracted with ethyl acetate. The organic phase was again washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/hexane). Yield: 90%

References:

US2010/234340,2010,A1 Location in patent:Page/Page column 23

61873-93-6 Synthesis