Hydrochloric Acid → 2-(2-Chloro-4-methoxy-phenyl)-1-quinoxalin-6-yl-ethanone

HRID 1096037Notes

Reaction equation

HRID 1096037 reaction equation
C([Mg]Cl)(C)(C)C.[Cl:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]([OH:19])=O.[N:20]1[C:29]2[C:24](=[CH:25][C:26](C(OC)=O)=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1.Cl>C(OCC)C.C1COCC1.O>[Cl:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]([C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[N:20]2)=[O:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2781239Methyl 6-quinoxalinecarboxylateHCID 42091322-(2-Chloro-4-methoxyphenyl)acetic acidHCID 178418310HCID 178418310, compound

Product 1

HCID 666992302-(2-Chloro-4-methoxy-phenyl)-1-quinoxalin-6-yl-ethanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 2M solution of tert-butylmagnesium chloride (CAS Reg. No. 677-22-5) in diethyl ether (5.9 ml) was added to 2-chloro-4-methoxyphenylacetic acid (1.173 g, CAS Reg. No. 91367-09-8) in THF (10 ml). The mixture was stirred at room temperature for 30 min. A solution of methyl 6-quinoxalinecarboxylate (1 g, CAS Reg. No. 23088-23-5) in THF (3 ml) was added and the resulting mixture was stirred overnight. Aqueous HCl (25%, 1.5 ml) and water (30 ml) were added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (480 mg) as a light brown solid. MS (m/e)=313.2 [M+H+].

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-78c6a77ec643475aa983ef69075b0406
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

Loading…