Ethanol → HCID 12083038, compound

HRID 1168511Notes

Reaction equation

HRID 1168511 reaction equation
C(O)C.C(O[CH:7]([CH:19]1[C:28]2[N:27]=[CH:26][C:25]([CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)[CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11]CC)=O)C>C(N(CC)CC)C>[N:30]1([CH2:29][C:25]2[CH:24]=[C:23]3[C:28]4[N:27]([CH:26]=2)[C:9](=[O:11])[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][C:19]=4[CH2:20][CH2:21][CH2:22]3)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 702EthanolHCID 12083037HCID 12083037, compound

Product 1

HCID 12083038HCID 12083038, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 250 mL round bottom flask equipped with a condenser is charged with ethanol (150 mL), triethylamine (0.93 mL) and diethyl 2-(ethoxy(3-(morpholin-4-ylmethyl)-5,6,7,8-tetrahydroquinolin-8-yl)methyl)malonate (Preparation 17, 750 mg). The solution is heated to reflux. After 12 h, the mixture is concentrated to give a yellow solid, which is purified by flash chromatography (silica gel, 6% MeOH: methylene chloride) to give 603 mg of the title compound. Physical characteristics: 1H NMR (DMSO-d6): δ9.02, 8.04, 7.58, 4.24, 3.59, 3.57, 3.01, 2.88, 2.42, 1.89, 1.30; 13C NMR (DMSO-d6): δ165.3, 154.1, 141.6, 138.3, 134.4, 132.8, 126.9, 125.3, 110.0, 104.3, 66.1, 59.7, 59.1, 52.9, 29.2, 27.8, 20.7, 14.3; IR (KBr) 3079, 3037, 2958, 2931, 2913, 2850, 2828, 1731, 1679, 1647, 1628, 1600, 1509, 1462, 1450, 1297, 1270, 1251, 1227, 1206, 1114, 1097, 1079; HRMS m/z 357.1818.

Workup

  1. customA 250 mL round bottom flask equipped with a condenser
  2. temperatureThe solution is heated to reflux
  3. concentrationthe mixture is concentrated
  4. customto give a yellow solid, which
  5. customis purified by flash chromatography (silica gel, 6% MeOH: methylene chloride)

Sources & evidence

ORD record
ord-1c6f69a65e4f41029ddd11c5c8cda1af
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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