Water → HCID 66625866, compound

HRID 2167248Notes

Reaction equation

HRID 2167248 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([OH:13])[CH2:7][CH:8]([CH3:12])[NH:9]2)=[CH:4][CH:3]=1.[C:14](Cl)(=[O:16])[CH3:15].[OH2:18].N1[CH:24]=[CH:23]C=CC=1>ClCCl>[C:14]([N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=2)[CH:6]([O:13][C:23](=[O:18])[CH3:24])[CH2:7][CH:8]1[CH3:12])(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 66625696HCID 66625696, compound

Product 1

HCID 66625866HCID 66625866, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Step 2) 860 mg of 7-fluoro-4-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline as a brown oily substance was dissolved in 0.5 mL of pyridine and 10 mL of dichloromethane, and 16 mg of acetyl chloride was added to the solution under ice cooling. The mixture was stirred for 1.5 hours. After completion of the reaction, water was added to the reaction liquid, and the mixture was extracted with chloroform. Subsequently, the organic layer was dehydrated over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (ethyl acetate:hexane=1:2), and thus 1.4 g (100%) of 1-acetyl-7-fluoro-4-acetoxy-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as an oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionthe mixture was extracted with chloroform
  3. concentrationwas concentrated under reduced pressure
  4. customThe resulting residue was purified

Sources & evidence

ORD record
ord-5639991827e9428c8ba3d1ef60c53dc6
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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