Ethoxyquin → 2,2,4-Trimethyl-1,2-dihydro-6-quinolinol

HRID 25795

반응식

HRID 25795 반응식
C([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:15])([CH3:14])[CH:8]=[C:7]2[CH3:16])C.B(Br)(Br)Br>ClCCl>[CH3:14][C:9]1([CH3:15])[CH:8]=[C:7]([CH3:16])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([OH:3])[CH:5]=2)[NH:10]1

참가 물질

4

반응물 2

HCID 3293EthoxyquinHCID 25134Boron tribromide2회

생성물 1

HCID 5997992,2,4-Trimethyl-1,2-dihydro-6-quinolinol수율 45.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 31 g of 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline in 300 mL of dichloromethane was treated with 30 mL of boron tribromide dropwise at −78° C. After the addition of boron tribromide, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into crushed ice and the pH was adjusted to 9 with sodium bicarbonate. The product was the extracted into EtOAc. The organic solution was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by filtering through a short plug of silica gel eluting with 25% EtOAc in hexanes solution to give 12.4 g of 2,2,4-trimethyl-1,2-dihydroquinolin-6-ol as a light brown solid.

후처리

  1. customthe cooling bath was removed
  2. additionThe reaction mixture was then poured
  3. custominto crushed ice
  4. extractionextracted into EtOAc
  5. washThe organic solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. filtrationby filtering through a short plug of silica gel eluting with 25% EtOAc in hexanes solution

출처 및 근거

ORD 기록
ord-b788bc3ae1e342adb325965bd12b86b8
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858627B2

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