Ethanol → HCID 19032349, compound

HRID 266136Notes

Reaction equation

HRID 266136 reaction equation
Cl[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]([CH3:29])[CH3:28])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:32][CH3:33])=[C:8]([O:30][CH3:31])[CH:9]=2)[N:4]=1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(O)C>ClCCl>[CH:27]([O:26][C:20]1[CH:19]=[C:18]([C:11]2[C:10]3[C:5](=[CH:6][C:7]([O:32][CH3:33])=[C:8]([O:30][CH3:31])[CH:9]=3)[N:4]=[C:3]([CH2:2][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:23]=[CH:22][C:21]=1[O:24][CH3:25])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 8083MorpholineHCID 10624326HCID 10624326, compound

Product 1

HCID 19032349HCID 19032349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-chloromethyl-4-(3-isopropoxy-4-methoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (3.0 g), morpholine (2.76 g) and ethanol (50 ml)--dichloromethane (5 ml) was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and dichloromethane (50 ml) was added to the residue. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (1:1, v/v) gave ethyl 4-(3-isopropoxy-4-methoxyphenyl)-6,7-dimethoxy-2-morpholinomethylquinoline-3-carboxylate as an oil. This oil was dissolved in ethanol (20 ml), and a solution of hydrogen chloride in ethanol (23%, 1.05 g) was added. The mixture was stirred at room temperature for 10 minutes, and the solvent was evaporated under reduced pressure. The crystals were separated by filtration and recrystallized from ethanol-ether to give ethyl 4-(3-isopropoxy-4-methoxyphenyl)-6,7-dimethoxy-2-morpholinomethylquinoline-3-carboxylate hydrochloride (1.62 g, 45%). Colorless crystals, mp. 185°-188° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and dichloromethane (50 ml)
  2. additionwas added to the residue
  3. washThe dichloromethane layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe fractions eluted with chloroform-ethyl acetate (1:1

Sources & evidence

ORD record
ord-4c7340c0fe864ccda2c98c1d92eb4d64
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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