Synthesis of 8-amino-6-methoxycinnoline. A precursor for 2-azaprimaquine

4-Methoxy-2-nitroaniline was converted in seven steps to 8-amino-6-methoxycinnoline with an overall yield of 33%. Several attempts to introduce a 5-aminopentan-2-yl side-chain in the amino-group to give 2-azaprimaquine were unsuccessful.