Resorcinol → 3-(6,7-Dimethoxy-quinolin-4-yloxy)-phenol

HRID 393629

Reaction equation

HRID 393629 reaction equation
[OH-].[K+].Cl[C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]=[CH:6][CH:5]=1.[OH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=1>>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:16][CH3:17])[N:7]=[CH:6][CH:5]=[C:4]2[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=1

Participants

4

Reactant 3

HCID 5054ResorcinolHCID 14797Potassium HydroxideHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 226465273-(6,7-Dimethoxy-quinolin-4-yloxy)-phenolYield 78%

Conditions

Temperature
140 °C

Procedure

Potassium hydroxide (14 mg, 0.25 mmol) and 4-chloro-6,7-dimethoxyquinoline (50 mg, 0.22 mmol), (prepared as described for the starting material in Example 2), were added to 1,3-dihydroxybenzene (1 g, 9 mmol) melted at 140° C. under argon. After stirring for 1 hour at 140° C., the mixture was partitioned between ethyl acetate and water and 2M hydrochloric acid was added to adjust the aqueous phase to pH4. The organic layer was washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was purified by column chromatography eluting with methylene chloridelethyl acetate (6/4 increasing to 3/7). The purified product was triturated with ether, collected by filtration and dried under vacuum to give 6,7-dimethoxy-4-(3-hydroxyphenoxy)quinoline (51 mg 78%).

Workup

  1. customthe mixture was partitioned between ethyl acetate and water and 2M hydrochloric acid
  2. additionwas added
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles were removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloridelethyl acetate (6/4 increasing to 3/7)
  8. customThe purified product was triturated with ether
  9. filtrationcollected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-a594f7f6d2cb45568f635c8842159098
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Linked notes

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