Triethylamine → HCID 54000465, compound

HRID 1757097Notes

Reaction equation

HRID 1757097 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[OH:16][C:17]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[NH:20][C:19](=O)[C:18]=1[N+:28]([O-:30])=[O:29].C(N(CC)CC)C>C(Cl)Cl>[N+:28]([C:18]1[C:19]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[N:20][C:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=2[C:17]=1[O:16][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:8])=[O:6])([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 546845154-Hydroxy-3-nitro-5,6,7,8-tetrahydroquinolin-2(1H)-one

Product 1

HCID 54000465HCID 54000465, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoromethanesulfonic anhydride (8.0 mL, 47 mmole) was added via a syringe to a cooled (0° C.) homogeneous mixture containing 5,6,7,8-tetrahydro-4-hydroxy-3-nitro-2(1H)-quinolinone (4.0 g, 19 mmole) and triethylamine (6.6 mL, 47 mmole) in methylene chloride (200 mL). The reaction mixture was stirred at 0° C. for 30 minutes. The reaction mixture was filtered through a layer of silica gel and the gel eluted with methylene chloride. The organic phase was evaporated under vacuum to provide 8.4 g of the desired product as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of silica gel
  2. washthe gel eluted with methylene chloride
  3. customThe organic phase was evaporated under vacuum

Sources & evidence

ORD record
ord-18874fdff4d849c8b72797313660a179
Source dataset
uspto-grants-1995_08
Patent number
US05444065

Reaction notes

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