HCID 18696619, compound → 7-Methoxynaphthalen-1-amine

Participants

Reaction Steps

To a solution of crude title compound of Step A (42.1 g) in diphenyl ether (320 mL) was added 10% palladium on carbon (17.8 g). The heterogeneous black mixture was heated at reflux for 5 h under N2 while stirring. The reaction mixture was allowed to cool to room temperature and filtered. The filtrate was acidified with concentrated HCl and the resulting white precipitate was collected by filtration, washed with CH2Cl2, dissolved in water and treated with 50% aqueous NaOH until basic. The aqueous mixture was then extracted four times with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered and the filtrate was concentrated under reduced pressure to give 20.9 g of the title compound of Step B as a pink solid melting at 79-80° C. 1H NMR (CDCl3): δ 7.70 (d,1H), 7.29-7.13 (m,3H), 7.07 (d,1H), 6.80 (dd,1H), 4.0 (br s,2H), 3.94 (s,3H).

Provenance & Evidence