Methyl 3-methoxy-4-(6-nitro-2,3-di-hydrobenz-1,4-oxazin-4-ylmethyl)benzoate → Methyl 4-(6-amino-2,3-dihydrobenz-1,4-oxazin4-ylmethyl)-3-methoxybenzoate

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Reaction Steps

Palladium-on-carbon (10% w/w, 0.2 g.) was added to a solution of (G) (0.69 g.) in ethyl acetate (50 ml.) in a hydrogenation bottle and the mixture hydrogenated at a pressure of 3.17 bars of hydrogen. When the uptake of hydrogen had ceased, catalyst was removed by filtration through diatomaceous earth. The filter pad was washed with ethyl acetate and the filtrate and washings were evaporated to give methyl 4-(6-amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)-3-methoxybenzoate (0.625 g., 91%) as a foam; NMR: 3.1 (br s,2 H, NH2), 3.3 (t,2 H, OCH2CH2N), 3.85 (m,6 H, OCH3 +CO2CH3), 4.2 (t,2 H, OCH2CH2N), 4.45 (s, 2 H, CH2 --Ar), 6.0 (m,2 H), 6.55 (d,1 H), 7.3 (d,1 H), 7.55 (m, 2 H).

Provenance & Evidence