Sodium Carbonate → HCID 135462828, compound

HRID 1954173Notes

Reaction equation

HRID 1954173 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]1[NH:19][N:18]=[N:17][N:16]=1)=[CH:7]2.[C:20](=O)([O-])[O-].[Na+].[Na+].[N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[CH2:36][O:37][CH:38](Cl)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41]C=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]1[N:19]=[N:18][N:17]([CH2:20][C:42]3[CH:43]=[CH:44][CH:39]=[C:38]([O:37][CH2:36][C:27]4[CH:28]=[CH:29][C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:26]=4)[CH:41]=3)[N:16]=1)=[CH:7]2.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]1[N:16]([CH2:20][C:42]3[CH:43]=[CH:44][CH:39]=[C:38]([O:37][CH2:36][C:27]4[CH:28]=[CH:29][C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:26]=4)[CH:41]=3)[N:17]=[N:18][N:19]=1)=[CH:7]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 23054691HCID 23054691, compoundHCID 178488102HCID 178488102, compound

Product 2

HCID 135462828HCID 135462828, compoundHCID 135484041HCID 135484041, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 6-methoxy-3-tetrazolyl-1,2-dihydroquinolin-2-one sodium salt (36.7 g, 138 mmol), sodium carbonate (14.7 g, 138 mmol), and tetra-n-butylammoniumbromide (22.3 g, 69.1 mmol), was added DMF (2 liters). (2-Quinolylmethoxy)benzyl chloride (58.7 g) was added to the resultant mixture, and the mixture was stirred for 15 hours at a bath temperature of 80° C. Subsequently, the solvent of the reaction mixture was removed under reduced pressure. To the obtained residue was added an 2N sodium hydroxide aqueous solution (1 liter). The organic phase was extracted from the solution with a mixture of chloroform-methanol (5:1). The organic phase was dried over sodium sulfate anhydrate, recrystallized from ethyl acetate, subjected to silica gel column chromatography (chloroform-methanol (5:1)), and concentrated under reduced pressure. The obtained residue was recrystallized from a chloroform-methanol-ether mixture, to thereby obtain crude 6-methoxy-3-{2-[3-(2-quinolylmethoxy)benzyl]-tetrazolyl}quinolin-2-one as first-deposited crystals, and crude 6-methoxy-3-{1-[3-(2-quinolylmethoxy)benzyl]-tetrazolyl}quinolin-2-one as second-deposited crystals.

Workup

  1. customSubsequently, the solvent of the reaction mixture was removed under reduced pressure
  2. additionTo the obtained residue was added an 2N sodium hydroxide aqueous solution (1 liter)
  3. extractionThe organic phase was extracted from the solution with a mixture of chloroform-methanol (5:1)
  4. dry with materialThe organic phase was dried over sodium sulfate anhydrate
  5. customrecrystallized from ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was recrystallized from a chloroform-methanol-ether mixture

Sources & evidence

ORD record
ord-b095a984bc0e4a61a3f0cec1a9330a58
Source dataset
uspto-grants-2000_09
Patent number
US06121286

Reaction notes

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