Hydrochloric Acid → 3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[C:12]([NH:13]C(=O)OC(C)(C)C)=[CH:11][N:10]([CH3:21])[N:9]=2)[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[C:12]([NH2:13])=[CH:11][N:10]([CH3:21])[N:9]=2)[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of tert-butyl 3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-ylcarbamate (543.2 mg, 1.608 mmol, 1 eq) was added hydrogen chloride (5.0 mL of a 4.0 M solution in 1,4-dioxane, 0.020 mol, 12 eq). The reaction mixture was stirred at room temperature for 9 hours and then evaporated to dryness. The solid residue was partitioned between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The aqueous portion was extracted once more with dichloromethane, and the combined organic extracts dried over magnesium sulfate and concentrated to give 3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-amine, which was carried forward without purification. LCMS (ESI) m+H=238.2; 1H NMR (400 MHz, CDCl3) δ: 7.53 (s, 1H), 7.28 (d, 1H), 7.02 (s, 1H), 6.91 (d, 1H), 3.91 (d, 2H), 3.87 (s, 3H), 3.84 (s, 3H).