Hydrochloric Acid → 8-Quinolinamine,1,2,3,4-tetrahydro-1-methyl-(9CI)

Anhydrous HCl (gas) was bubbled through a stirred solution of 1-methyl-8-(N-tert-butoxycarbonylamino)-1,2,3,4-tetrahydroquinoline (0.83 g, 3.16 mmol) in methanol (30 mL), at room temperature, for 10 minutes. The resultant solution was stirred at room temperature for 1 hour then concentrated under reduced pressure. The residue was partitioned between CH2Cl2 (50 mL) and aqueous NaOH (10 N, 10 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated to afford 0.468 g (88%) of 1-methyl-8-amino-1,2,3,4-tetrahydroquinoline as a white solid. 1H NMR (CDCl3) δ 1.83-1.91 (m, 2H), 2.69 (s, 3H), 2.78 (t, 2H, J=6.6 Hz), 3.07-3.11 (m, 2H), 3.84 (br s, 2H, NH2), 6.52 (d, 1H, J=7.5 Hz), 6.56 (d, 1H, J=7.5 Hz), 6.81 (dd, 1H, J=7.5, 7.5 Hz).

1. concentrationthen concentrated under reduced pressure
2. customThe residue was partitioned between CH2Cl2 (50 mL) and aqueous NaOH (10 N, 10 mL)
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
5. dry with materialThe combined organic extracts were dried (Na2SO4)
6. concentrationconcentrated

ORD record

ord-36a9d9b8eb294b11819b3553564cc0a6

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629337B2