Isopropyl chloroformate → HCID 54498760, compound

HRID 1857488Notes

Reaction equation

HRID 1857488 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[NH:8][CH:7]([CH3:16])[CH2:6][C:5]2=[O:17].Cl[C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20].[OH-].[K+]>ClCCl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH:22]([O:21][C:19]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([C:12]([F:14])([F:13])[F:15])[CH:10]=2)[C:5](=[O:17])[CH2:6][CH:7]1[CH3:16])=[O:20])([CH3:24])[CH3:23]

Participants

7

Reactant 3

HCID 7917Isopropyl chloroformateHCID 14797Potassium HydroxideHCID 22461140HCID 22461140, compound

Product 1

HCID 54498760HCID 54498760, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

6-Fluoro-2-methyl-4-oxo-7-trifluoromethyl-3,4-dihydro-2H-quinoline (1.01 g, 4.08 mmol) was dissolved in 10 mL of dichloromethane and 5 mL of pyridine, and stirred as isopropyl chloroformate (48 mL of a 1 molar solution in toluene, 48 mmol) was added slowly via syringe. After stirring overnight, 100 ml of a 1M aqueous potassium hydroxide solution was added and the aqueous phase was extracted with ethyl acetate (3×75 mL), the combined organics were washed with 1M HCl (2×50 mL), 100 mL each of a saturated sodium bicarbonate solution and brine, before being dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford 1.1 g of an oil, which was purified by chromatography on silica gel eluting with 10% ethyl acetate in hexanes to afford 940 mg (69%) of the title compound as an oil. 1H NMR (CDCl3) δ 1.24 (d, 3H), 1.34 (d, 3H), 1.38 (d, 3H), 2.65 (dd, 1H), 3.05 (dd, 1H), 5.1-5.3 (m, 2H),

Workup

  1. additionwas added slowly via syringe
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×75 mL)
  3. washthe combined organics were washed with 1M HCl (2×50 mL), 100 mL each of a saturated sodium bicarbonate solution and brine
  4. dry with materialbefore being dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-1455c950101f4fd0a9eb58cc05c3a70b
Source dataset
uspto-grants-2000_11
Patent number
US06147090

Reaction notes

Loading…