Chloroform → (2-Oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl acetate

HRID 1256274Notes

Reaction equation

HRID 1256274 reaction equation
C(Cl)(Cl)Cl.[OH:5][CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.[CH3:18][C:19](OC(C)=O)=[O:20].C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.CCN(CC)CC>[C:19]([O:5][CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1)(=[O:20])[CH3:18]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 533933487-(Hydroxymethyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 67321616(2-Oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

To a CHCl3 (30.0 mL) solution, the compound (670 mg) obtained in Step 52-1, Ac2O (536 μL), DMAP (20.0 mg) and Et3N (1.05 mL) were added under ice cooling and the mixture was stirred at room temperature for 45 minutes. To the reaction mixture, a saturated aqueous NaHCO3 solution was added and the solution was extracted three times with CHCl3. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60 N, mobile phase: MeOH/CHCl3=0/100 to 10/90; v/v) to obtain (2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl acetate (767 mg, a light yellow solid).

Workup

  1. extractionthe solution was extracted three times with CHCl3
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 60 N, mobile phase: MeOH/CHCl3=0/100 to 10/90; v/v)

Sources & evidence

ORD record
ord-23ad6f68307d457d86de3b1e26c30e43
Source dataset
uspto-grants-2013_06
Patent number
US08461182B2

Reaction notes

Loading…