一二三四区视频,亚洲少妇熟女色,日本久热无码视频网,欧美国产日韩大尺度,亚洲a视频,久久少妇一区二区,日韩999无码视频,刺激久久久久久久,啊啊啊啊不要啊在线

Welcome to chemicalbook!
Chinese English Japanese Germany Korea
010-86108875
Try our best to find the right business for you.
Do not miss inquiry messages Please log in to view all inquiry messages.

Welcome back!

ChemicalBook CAS DataBase List 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one
526-43-2

2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one synthesis

8synthesis methods
-

Yield:526-43-2 27%

Reaction Conditions:

Stage #1: 1,2,3,4-tetrahydronorharman-1-onewith trichlorophosphate in tetrahydrofuran at 60; for 3 h;Inert atmosphere;
Stage #2: Methyl N-methylanthranilate in tetrahydrofuran at 75; for 96 h;Inert atmosphere;Further stages;

Steps:

1.1 4.1.1. 2-[2-(Methylamino)benzoyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (2b).

To a stirred solution of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (190 mg, 1.01 mmol, 1.0 equiv) in dry THF (15 mL), POCl3 (0.13 mL, 1.42 mmol, 1.4 equiv) was added and the mixture was stirred under Ar atmosphere for 3 h at 60 °C. Then, N-methylanthranilate (280 mg, 1.69 mmol, 1.7 equiv) was added, the temperature increased to 75 °C and the mixture stirred for 96 h. The solution was cooled to rt, CH2Cl2 and 2M NaOH were added (pH=13). The water layer was removed and the remaining orange colored organic layer was acidified with 2M HCl (pH=2). By this the color disappeared and water was added. The organic phase was removed and 2M NaOH was added to the water phase. The water phase was extracted three times with CH2Cl2 (3*30 mL) and dried over Na2SO4. The solvent was evaporated and the remaining brownish oil was kept in the freezer. Upon warming it to rt light yellowish crystals formed. The crystals were filtered off and washed tree times with diethyl ether. A yellow solid was formed during washing. This was dried and then washed as above. This yielded an orange solid (89.4 mg, 0.28 mmol, 27%). Rf=0.20 (SiO2, 100% ethyl acetate). Mp=170.7-173.0 °C. 1H NMR (400 MHz, CDCl3, 300 K): δ=10.12 (s, 1H, NHindole), 7.63-7.61 (m, 1H, Ar-HE-ring), 7.44 (dd, J=8.0, 1.6 Hz, 1H, Ar-HA-ring), 7.38-7.34 (m, 1H, Ar-HA-ring), 7.30-7.23 (m, 1H, Ar-HE-ring), 7.19 (d, J=5.1 Hz, 1H, NHCH3) 7.17-7.13 (m, 1H, Ar-HE-ring), 7.09 (d, J=8.3 Hz, 1H, Ar-HE-ring), 6.77 (dd, J=8.6, 1.0 Hz, 1H, Ar-HA-ring), 6.53-6.49 (m, 1H, Ar-HA-ring), 4.19 (t, J=6.5 Hz, 2H, NCH2CH2), 3.20 (t, J=6.5 Hz, 2H, NCH2CH2), 2.95 (d, J=4.8 Hz, 3H, CH3) ppm. 13C{1H} NMR (101 MHz, CDCl3, 300 K): δ=175.98 (s, C=O), 162.27 (s, C=O), 151.15 (s, Cquart.), 151.05 (s, Cquart.), 138.70 (s, Cquart.), 134.66 (s, Ar-C), 132.50 (s, Ar-C), 126.24 (s, Ar-C), 124.83 (s, Cquart.), 122.94 (s, Cquart.), 120.71 (s, Ar-C), 120.67 (s, Ar-C), 115.90 (s, Cquart.), 114.73 (s, Ar-C), 113.16 (s, Ar-C), 111.22 (s, Ar-C), 47.64 (s, NCH2CH2), 29.89 (s, CH3), 21.29 (s, NCH2CH2) ppm. IR: ν=3403w, 3264m, 2811w, 2371w, 2357w, 2349w, 1662s, 1605m, 1574m, 1551m, 1511m, 1487m, 1424w, 1395m, 1368w, 1321m, 1287m, 1265w, 1243w, 1231m, 1202m, 1174m, 1128w, 1107w, 1093w, 1067w, 1047m, 1003w, 993w, 980w, 946m, 892m, 851w, 803w, 776w, 768m, 747s, 740s, 712m, 676w, 659m cm-1. HPLC: Synergi 4U fusion-RP (15*0.46 cm), water/methanol (30-95%), 0.1% formic acid, 1.00 mL/min, 20 °C, tR=4.537 min, purity=95.30%. Mass: calcd for [M+H]+ (C19H18N3O2) requires m/z: 320.14 (open), 302.13 (closed); found: 302.20.

References:

Wehle, Sarah;Espargaró, Alba;Sabaté, Raimon;Decker, Michael [Tetrahedron,2016,vol. 72,# 20,p. 2535 - 2543]

2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one Related Search:

延庆县| 葫芦岛市| 邢台市| 台东县| 安吉县| 渑池县| 淅川县| 信丰县| 海盐县| 九龙城区| 林口县| 枣强县| 永清县| 博客| 洛浦县| 福泉市| 修武县| 卓资县| 美姑县| 绥宁县| 临泽县| 永顺县| 河北区| 湘潭县| 安泽县| 合作市| 汾西县| 米易县| 云梦县| 元谋县| 临沭县| 兰州市| 建阳市| 灌云县| 新化县| 三台县| 大连市| 庆元县| 资兴市| 封丘县| 青岛市|