Propanal → 4-Methoxybenzylamine

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Reaction Steps

2-Bromo-5-methyl nicotinic acid ethyl ester, depicted by formula 31 in Scheme 12, was used as a starting material to prepare compounds with methyl substitution at 6-position of naphthyridine moiety. This starting material was prepared by condensation of propionaldehyde with ethyl cyanoacetate followed by cyclisation of resulted intermediate as shown in Scheme 12. Amination of 2-bromo-5-methyl nicotinic acid ethyl ester by p-methoxy benzyl amine gave 5-methyl-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester, depicted by formula 32 in Scheme 12, which was then converted into 6-methyl-1-(4-methoxy-benzyl)-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione, depicted by formula 33 in Scheme 12, by reacting with trichloromethyl chloroformate as shown in Scheme 12.

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