4-AMINO-2-CHLOROQUINOLINE

Preparation of compound 9 is described elsewhere [von Btichi, J. et al. Die Tuberkulostatische Wirkung von 2-Oxy-4-amino-chinolin Derivaten. HeIv. Chim. Acta. 1949, 32, 1806-1814; Wojahn, H. Untersuchungen ber den Zusammenhang von chemischer Konstitution und anasthesierender Wirkung bei 2-Alkoxy-chinolin Deivaten. Arch. Pharm. 1936, 274, 83-106]. However, we prepared compound 9 as described here. In brief, compound 8 (0.35 g, 1.8 mmol) was suspended in ammonia (28-30percent in water, 3 mL). The reaction was carried out in the microwave at 160 General procedure: The 2-chloro-4-azido quinolines (4mmol) compound 2(a–f) was taken in 20mL methanol and (4mmol) of sodium dithionite was added and refluxed for 3–6h on water bath. After the completion of reaction as it indicated by TLC spot change, the reaction mixture was poured into crushed ice, filtered, dried and chromatographed over silica gel using petroleum ether: ethyl acetate (80:20) (v/v) as eluent which pure light yellow/white colored needles compound 3(a–f). It was recrystallised from absolute methanol. 2.3.1 2-Chloroquinoline-4-amine (3a) Yield: 91percent; white needles; mp 180–183°C. IR (KBr, cmGeneral procedure: The 2-chloro-4-azido quinolines (4mmol) compound 2(a-f) was taken in 20mL methanol and (4mmol) of sodium dithionite was added and refluxed for 3-6h on water bath. After the completion of reaction as it indicated by TLC spot change, the reaction mixture was poured into crushed ice, filtered, dried and chromatographed over silica gel using petroleum ether: ethyl acetate (80:20) (v/v) as eluent which pure light yellow/white colored needles compound 3(a-f). It was recrystallised from absolute methanol. 2.3.1 2-Chloroquinoline-4-amine (3a) Yield: 91%; white needles; mp 180-183C. IR (KBr, cm-1): 1643, 2970, 3182, 3312, 3459. 1H NMR (400MHz, DMSO-d6): delta 6.51 (s, 1H, Ar-H), 7.17(s, 2H, NH2), 7.46-7.42 (m, 1H, Ar-H), 7.70-7.63(m, 2H, Ar-H), 8.17 (s, 1H, Ar-H). 13C NMR (100MHz, DMSO-d6): delta 100.50, 117.63, 122.44, 124.29, 127.89, 130.24, 147.99, 150.55, 154.13. ESI-MS (m/z): calcd for [M+H]+ 178.62, found 179.00; Anal. Calcd for C9H7ClN2: C, 60.52; H, 3.95; N, 15.68 Found: C, 60.56; H, 3.89; N, 15.70.Preparation of compound 9 is described elsewhere [von Btichi, J. et al. Die Tuberkulostatische Wirkung von 2-Oxy-4-amino-chinolin Derivaten. HeIv. Chim. Acta. 1949, 32, 1806-1814; Wojahn, H. Untersuchungen ber den Zusammenhang von chemischer Konstitution und anasthesierender Wirkung bei 2-Alkoxy-chinolin Deivaten. Arch. Pharm. 1936, 274, 83-106]. However, we prepared compound 9 as described here. In brief, compound 8 (0.35 g, 1.8 mmol) was suspended in ammonia (28-30% in water, 3 mL). The reaction was carried out in the microwave at 160 0C for 2.5 hours. After the reaction was completed, ammonia was evaporated off. The product was purified by column chromatography, eluent 3% MeOH in DCM. Yield: 0.14 g (44%). 1H NMR (CDCl3) delta 4.83 (bs, 2H, NH2), 6.62 (s, IH, Ar), 7.43-7.51 (m, IH, Ar), 7.63-7.73 (m, 2H, Ar), 7.89-7.95 (m, IH, Ar). 13C NMR (600MHz, CDCl3) delta 103.07, 117.60, 120.08, 125.27, 129.13, 130.46, 148.26, 151.40, 151.41.

Molecular Weight:178.62
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:178.0297759
Monoisotopic Mass:178.0297759
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes