Sodium Hydroxide → 5,6-Dichloro-2-methyl-4-oxo-1,2,3,4-tetra-hydroquinoline

HRID 2413958

반응식

HRID 2413958 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[NH:5][CH:6]([CH3:11])[CH2:7][C:8]([OH:10])=O.[OH-].[Na+]>O>[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:4]2[C:3]=1[C:8](=[O:10])[CH2:7][CH:6]([CH3:11])[NH:5]2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 2948103-(3,4-Dichloroanilino)butanoic acid

생성물 1

HCID 201543515,6-Dichloro-2-methyl-4-oxo-1,2,3,4-tetra-hydroquinoline수율 10.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

300 g of polyphosphoric acid was added to 99.24 g (0.40 mole) of the 3-(3,4-dichloroanilino)butyric acid and this mixture was stirred at 90°-100° C. for 4 hours. After being allowed to cool to room temperature, the resulting reaction solution was diluted with 3 liters of water and then adjusted to pH 4-5 with an aqueous sodium hydroxide solution. Then, the solid matter which separated out was extracted with chloroform and this extract was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (using chloroform as the developing solvent). The fraction containing the desired product was evaporated to dryness under reduced pressure and the resulting residue was recrystallized from benzene to obtain 9.94 g (10.8% yield) of 5,6-dichloro-2-methyl-4-oxo-1,2,3,4-tetra-hydroquinoline in the form of yellow crystals. On the other hand, another fraction was worked up in the same manner as above to obtain 13.53 g (14.7% yield) of a structural isomer thereof, or 6,7-dichloro-2-methyl- 4-oxo-1,2,3,4-tetrahydroquinoline, in the form of yellow crystals.

후처리

  1. customthe resulting reaction solution
  2. customThen, the solid matter which separated out
  3. extractionwas extracted with chloroform
  4. concentrationthis extract was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography (
  7. additionThe fraction containing the desired product
  8. customwas evaporated to dryness under reduced pressure
  9. customthe resulting residue was recrystallized from benzene

출처 및 근거

ORD 기록
ord-3513d2b106d34c8da59f6164e403d1f1
출처 데이터셋
uspto-grants-1988_01
특허 번호
US04720495

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