Hydrochloric Acid → HCID 22007426, compound

HRID 613014Notes

Reaction equation

HRID 613014 reaction equation
[O:1]=[C:2]1[CH:11]=[C:10]([C:12]([O:14]C(C)(C)C)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:19]1[CH:24]=[C:23]([C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:37][CH3:38])=[C:32]([O:35][CH3:36])[CH:33]=3)[CH:28]=[C:27]([CH2:39][OH:40])[C:26]=2[CH2:41][OH:42])[CH:22]=[CH:21][N:20]=1.Cl>O1CCOCC1>[O:1]=[C:2]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:19]1[CH:24]=[C:23]([C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:37][CH3:38])=[C:32]([O:35][CH3:36])[CH:33]=3)[CH:28]=[C:27]([CH2:39][OH:40])[C:26]=2[CH2:41][OH:42])[CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15870506HCID 15870506, compound

Product 1

HCID 22007426HCID 22007426, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-[2-(2-Oxo-4-tert-butoxycarbonyl-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (0.96 g) is added to a 4 M solution of hydrogen chloride in dioxane (25 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. The mixture is concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; chloroform:methanol:acetic acid=90:10:3), and crystallized from ethyl acetate to give 1-[2-(2-oxo-4-carboxy-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (0.41 g) which is listed in Table 7.

Workup

  1. temperaturecooling
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove the solvent
  4. customthe residue is purified by silica gel column chromatography (solvent; chloroform:methanol:acetic acid=90:10:3)
  5. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fcf3163d49c440fc92486563f3697e26
Source dataset
uspto-grants-1999_12
Patent number
US06005106

Reaction notes

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