CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2.CC(C)([O-])C.[K+].C[N:25]1CCCC1=O.[NH2:31][O:32][S:33]([OH:36])(=[O:35])=[O:34].CN1CCCC1=O>CN1CCCC1=O>[NH2:31][O:32][S:33]([OH:36])(=[O:35])=[O:34].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([NH2:25])[CH:13]=[CH:12]2A solution of 10.0 g (9.7 g corrected for 97% purity) of hydroxylamine-O-sulfonic acid (HOSA) in 33.7 g of N-methylpyrrolidinone (NMP) is prepared and chilled to 0–5° C. A second solution is prepared from 20.1 g (19.1 g corrected for 95% purity) of potassium tert-butoxide and 34.4 g of NMP. An amination vessel is charged with 5.9 g of 5-methoxyindole, 17.8 g of NMP and an initial charge of 0.7 g of the potassium tert-butoxide/NMP solution. The HOSA/NMP solution and the remaining potassium tert-butoxide/NMP solution are then simultaneously and proportionally metered into the amination vessel over a period of 86 minutes while maintaining a reaction temperature of 15–22° C. to yield a solution containing 5.6 g (87% yield) of 5-methoxy-1H-indol-1-amine as determined by internal standard HPLC assay.
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