\text{HNO}_3 / \text{H}_2\text{SO}_4; 2) \text{H}_2, \text{Pd/C}; 3) \text{CH}_3\text{Br}(2당량)

\text{Br}_2, \text{FeBr}_3; 2) \text{NH}_3 (excess), heat; 3)\text{CH}_3\text{I} (excess), \text{K}_2\text{CO}_3

\text{CH}_3\text{Cl}, \text{AlCl}_3; 2) \text{NaNH}_2, \text{NH}_3; 3) \text{NaBH}_4

\text{HNO}_3 / \text{H}_2\text{SO}_4; 2)\text{ Fe, HCl}; 3) \text{CH}3\text{I} (excess), \text{Ag}_2\text{O}

\text{CH}_3\text{COCl}, \text{AlCl}_3 2) \text{Wolff-Kishner} (\text{NH}_2\text{NH}_2, \text{KOH}, \text{heat}); 3) \text{formaldehyde}, \text{NaBH}_3\text{CN}