Potassium Carbonate → HCID 9956212, compound

HRID 1493499Notes

Reaction equation

HRID 1493499 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C[C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].[C:22](=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[CH3:22][O:3][C:1](=[O:4])[CH2:2][C:8]1[CH:9]=[C:10]([O:12][CH2:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=2)[CH:11]=[CH:6][C:7]=1[NH:13][C:14]1[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 67868427HCID 67868427, compound

Product 1

HCID 9956212HCID 9956212, compound

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

Under an atmosphere of nitrogen, a mixture of the crude phenol of Step F, above (5.0 g, 15.4 mmol), potassium carbonate (1.3 g, 9.8 mmol), 18-crown-6 (130 mg), and 2-chloromethyl quinoline (4.1 g, 23 mmol) in 50 mL of acetonitrile is stirred at 60° C. for 24 hours (TLC, silica, dichloromethaneMeOH 19:1). The solvent is evaporated and the residue partitioned between ethyl acetate and water (75 mL each). The insolubles are filtered, the layers separated and the organic phase washed with 1N NaOH and brine. After drying (MgSO4) the solvent is removed in vacuo to give 7.0 g of a thick brown oil. The crude product is purified by flash chromatography (silica Merck 60, dichloromethane and dichloromethane-ethyl acetate 19:1) to give the product (4.2 g, clear oil). The oil is triturated with ethanol to give crystalline product (3.98 g, 55.5%, m.p. 90°-91° C., white solid).

Workup

  1. customThe solvent is evaporated
  2. customthe residue partitioned between ethyl acetate and water (75 mL each)
  3. filtrationThe insolubles are filtered
  4. customthe layers separated
  5. washthe organic phase washed with 1N NaOH and brine
  6. dry with materialAfter drying (MgSO4) the solvent
  7. customis removed in vacuo

Sources & evidence

ORD record
ord-1deed4e3ab034980b46a319222285040
Source dataset
uspto-grants-1991_06
Patent number
US05021576

Reaction notes

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