Hydrochloric Acid → HCID 54706315, compound

HRID 1740633Notes

Reaction equation

HRID 1740633 reaction equation
[O:1]=[C:2]1[CH:11]=[C:10]([O:12]COC)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:16]1[CH:21]=[C:20]([C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=3)[CH:25]=[C:24]([CH2:36][OH:37])[C:23]=2[CH2:38][OH:39])[CH:19]=[CH:18][N:17]=1.Cl>O1CCOCC1.CO>[O:1]=[C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:16]1[CH:21]=[C:20]([C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=3)[CH:25]=[C:24]([CH2:36][OH:37])[C:23]=2[CH2:38][OH:39])[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22007450HCID 22007450, compound

Product 1

HCID 54706315HCID 54706315, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

1-[2-(2-Oxo-4-methoxymethoxy-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (1.39 g) is dissolved in a mixture of dioxane (10 ml) and methanol (5 ml), and thereto is added 2M hydrochloric acid (2 ml). The mixture is warmed to 50° C., and stirred for 7 hours, and then concentrated under reduced pressure to remove the solvent. To the residue are added chloroform and water, and the chloroform layer is separated, washed, dried and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1) to give 1-[2-(2-oxo-4-hydroxy-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (0.79 g) which is listed in Table 7.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the solvent
  3. additionTo the residue are added chloroform and water
  4. customthe chloroform layer is separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-e279a451888d413b9be0b286c582465a
Source dataset
uspto-grants-1999_10
Patent number
US05969140

Reaction notes

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