Ethanolamine → HCID 18432983, compound

HRID 2305483Notes

Reaction equation

HRID 2305483 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)[CH:3]=1.[CH2:22]([CH2:24][NH2:25])[OH:23].O.Cl.CCOCC>C(OCC)(=O)C.CO>[ClH:1].[CH2:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][N:12]1[C:4]1[CH:3]=[C:2]([NH:25][CH2:24][CH2:22][OH:23])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 962Water2×HCID 10953452Ether hydrochlorideHCID 18433086HCID 18433086, compound

Product 1

HCID 18432983HCID 18432983, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
155 °C

Procedure

4-Chloro-2-(3,4-dihydro-1H-isoquinolin-2-yl)-quinoline (0.5 g, 1.7 mmol) and ethanolamine (0.61 ml, 10.2 mmol) were mixed and heated at 150-160° C. for 16 hours. The reaction mixture was cooled to room temperature and water (20 ml) was added. After decantation of water, the gummy residue was dissolved in ethyl acetate, dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed over silica gel (CH2Cl2—MeOH, 9:1 then 4:1) to provide a white foam which was dissolved in MeOH (5 ml). HCl-Et2O was added to provide 2-[2-(3,4-dihydro-1H-isoquinolin-2-yl)-quinolin-4-ylamino]-ethanol hydrochloride (0.16 g, 27%) as a white solid, m.p. 130-140° C. and MS: m/e=320.3 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was chromatographed over silica gel (CH2Cl2—MeOH, 9:1
  5. custom4:1) to provide a white foam which

Sources & evidence

ORD record
ord-0de84dc8653b4ceb88eca7dee9897480
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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