Water → HCID 9802280, compound

HRID 1791694Notes

Reaction equation

HRID 1791694 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:28][C:29]1[CH:38]=[C:37]2[C:32]([CH:33]=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1.O>CS(C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[N:5]=[CH:4][N:3]=[C:2]2[O:28][C:29]1[CH:38]=[C:37]2[C:32]([CH:33]=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22030960HCID 22030960, compoundHCID 1354268667-Hydroxyquinoline

Product 1

HCID 9802280HCID 9802280, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazoline (200 mg, 0.64 mmol), potassium carbonate (102 mg, 0.74 mmol) and 7-hydroxyquinoline (107 mg, 0.74 mmol) in DMSO (5 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature. The mixture was poured into water, washed with dichloromethane and extracted twice with a 10/1 mixture of dichloromethane/methanol. The extracts were washed with water and brine, dried over magnesium sulphate, filtered and the filtrate evaporated under vacuum. The residue was purified by silica column chromatography, eluting with dichloromethane/methanol/0.880 aqueous ammonia (100/8/1) to give an oil which crystallised on trituration with ether to give 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)-4-(quinolin-7-yloxy)quinazoline (148 mg, 55%).

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with dichloromethane
  3. extractionextracted twice with a 10/1 mixture of dichloromethane/methanol
  4. washThe extracts were washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate evaporated under vacuum
  8. customThe residue was purified by silica column chromatography
  9. washeluting with dichloromethane/methanol/0.880 aqueous ammonia (100/8/1)
  10. customto give an oil which
  11. customcrystallised on trituration with ether

Sources & evidence

ORD record
ord-d3eddadf507f41a091a405d3f00e1f6e
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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