Sodium Carbonate → 7-Methoxy-3-methylquinoxalin-2(1H)-one

HRID 1644455Notes

Reaction equation

HRID 1644455 reaction equation
Cl[C:2]1[C:3]([CH3:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.C(=O)([O-])[O-:16].[Na+].[Na+]>Cl.O>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5]([N:4]=[C:3]([CH3:14])[C:2](=[O:16])[NH:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 467413403-Chloro-6-methoxy-2-methylquinoxaline2×

Product 1

HCID 217964227-Methoxy-3-methylquinoxalin-2(1H)-oneYield 71%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 3-chloro-6-methoxy-2-methylquinoxaline (Intermediate 162, 1.5 g, 7.21 mmol) in 5M HCl (30 mL) was heated to 110° C. for 1 hour. The reaction mixture was neutralized with saturated sodium carbonate solution, diluted with water and extracted with ethyl acetate (3 times). The combined organic phases were dried over magnesium sulfate and concentrated to a small volume under reduced pressure. The precipitate was collected by filtration to give 1.0 g (71%) of product as an off-white solid.

Workup

  1. extractionextracted with ethyl acetate (3 times)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated to a small volume under reduced pressure
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5996a36963e340f0a317dd8b7d07037f
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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