[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9](S(O)(=O)=O)[CH:8]=[CH:7]2.[NH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[CH:25]=[C:24]([OH:27])[CH:23]=[CH:22]2.[H-].[Na+].CI>CN(C)C=O.O>[NH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[CH:25]=[C:24]([OH:27])[CH:23]=[CH:22]2.[CH3:24][O:27][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[NH2:1])=[CH:7][CH:8]=1
8-Amino-naphthalen-2-ol was prepared from 8-amino-2-naphthalenesulphonic acid (commercially available) according to the literature (J. Org. Chem. 1949, p351). To a solution of 8-amino-naphthalen-2-ol (8.00 g) in dry N,N-dimethylformamide (80 mL) was added sodium hydride (60% dispersion in mineral oil, 3.2 g) carefully. After stirring for 4 hours the reaction mixture was cooled in an ice bath and methyl iodide (3.13 mL) was added dropwise. The reaction mixture was then stirred at room temperature for 3 days. Water (10 mL) was then added and the volatiles were removed in vacuo. The residue was dissolved in chloroform, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield a dark oil. This was purified using flash chromatography (chloroform) to yield 7-methoxy-naphthalen-1-ylamine as a dark brown liquid (2.92 g).
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