Sodium Carbonate → 7-Methoxy-3-(4-(methoxycarbonyl)phenyl)quinoline 1-oxide

HRID 1472697Notes

Reaction equation

HRID 1472697 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[CH:9]=[N:10]2)=[CH:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:31])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[CH:9]=[N+:10]2[O-:31])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67974241Methyl 4-(7-methoxyquinolin-3-yl)benzoate

Product 1

HCID 679742567-Methoxy-3-(4-(methoxycarbonyl)phenyl)quinoline 1-oxideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-(7-methoxyquinolin-3-yl)benzoate (632 mg, 2.16 mmol), mCPBA (742 mg, 4.31 mmol) and DCM (10 mL) was stirred overnight. Saturated Na2CO3 solution was added and adjusted the pH >7, the organic layer was washed with water (50 mL×2), dried over NaSO4 and evaporated in vacuo to give the crude product as a yellow solid (540 mg, 81.0%).

Workup

  1. washthe organic layer was washed with water (50 mL×2)
  2. dry with materialdried over NaSO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c82bbd33bd79474ab68e5828b6f6f47b
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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