O-Toluidine → HCID 70664909, compound

HRID 1403562Notes

Reaction equation

HRID 1403562 reaction equation
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[NH2:23][C:24]1[C:25]([CH3:30])=[CH:26][CH:27]=[CH:28][CH:29]=1>>[C:25]1([CH3:30])[C:24]([NH:23][C:2]2[C:3]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 7242O-ToluidineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 70664909HCID 70664909, compoundYield 37%

Procedure

Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (300 mg, 0.95 mmol) was stirred in o-toluidine (10 mL) at 145° C. for 3 days in an oil bath. The reaction mixture was concentrated in vacuo to give a residue, which was purified by a silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford methyl 3-(o-toluidino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a light yellow solid (145 mg, 37%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a residue, which
  3. customwas purified by a silica gel column chromatography (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-8821e0661b894e6586aa404206e0c2c1
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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