Pyridine → 2-Oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonate

HRID 1256275Notes

Reaction equation

HRID 1256275 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[O:19](S(C(F)(F)F)(=O)=O)[S:20]([C:23]([F:26])([F:25])[F:24])(=O)=[O:21]>C(Cl)(Cl)Cl>[F:24][C:23]([F:26])([F:25])[S:20]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1)(=[O:21])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 594607892-Oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
15 °C

Procedure

Step R1-1: To a suspension of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (200 g) in CHCl3 (2.0 L) was added pyridine (212 g) at room temperature over 10 minutes. Tf2O (344 g) was added to the mixture over 35 minutes, keeping the temperature below 10° C. After the mixture was allowed to warm to 15° C. over 1 hour, the reaction mixture was cooled to 0° C. and quenched by addition of water (2.0 L). The organic layer was separated, washed with aqueous saturated KHSO4 and water twice, dried over Na2SO4 and concentrated to obtain 2-oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonate as a pale yellow solid (346 g).

Workup

  1. customthe temperature below 10° C
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customquenched by addition of water (2.0 L)
  4. customThe organic layer was separated
  5. washwashed with aqueous saturated KHSO4 and water twice
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4ba5822876664c98b476f67b52d97eec
Source dataset
uspto-grants-2013_06
Patent number
US08461182B2

Reaction notes

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