Hydrochloric Acid → HCID 49757564, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[C:4]([NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH3:22])[CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH3:22])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl 6-chloro-4-[(2-propoxyethyl)amino]pyridin-3-ylcarbamate (7.08 g, 21.4 mmol) in 1,4-dioxane (20 mL) was treated with 4N HCl in 1,4-dioxane (100 mL) and stirred at room temperature for one hour. The reaction was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give 6-chloro-N4-(2-propoxyethyl)pyridine-3,4-diamine as a brown oil. (4.93 g, 100% yield). 1H NMR (CDCl3) δ 7.63 (1H), 6.45 (1H), 4.67 (1H), 3.67 (2H), 3.43 (2H), 3.32-3.27 (2H), 2.92 (2H), 1.64-1.55 (2H), 0.93 (3H).