Triethylamine → HCID 178481583, compound

HRID 1402769Notes

Reaction equation

HRID 1402769 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[NH2:9].C(N(CC)CC)C.[C:28](Cl)(=[O:32])[C:29](Cl)=[O:30]>C(Cl)Cl>[OH:30][C:29]1[C:28](=[O:32])[N:2]([CH3:1])[C:3]2[C:8]([N:9]=1)=[CH:7][CH:6]=[C:5]([C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=1)[CH:4]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86641377HCID 86641377, compound

Product 1

HCID 178481583HCID 178481583, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N3-methyl-4′-(trifluoromethoxy)biphenyl-3,4-diamine (1 g) in methylene chloride (35 ml) was cooled in an ice bath, and triethylamine (1.5 ml) was added, followed by dropwise addition of oxalyl chloride (670 mg). After 1 hour the solvent was removed under reduced pressure, and the residue was crystallized from methanol, to provide 3-hydroxy-1-methyl-7-(4-(trifluoromethoxy)phenyl)quinoxalin-2(1H)-one (550 mg).

Workup

  1. customAfter 1 hour the solvent was removed under reduced pressure
  2. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-f48734cceec442eaa32bde55b28f4fde
Source dataset
uspto-grants-2014_12
Patent number
US08912190B2

Reaction notes

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