Dimethylformamide → 2-Methyl-8-(2-oxopropoxy)quinoline

HRID 263970

반응식

HRID 263970 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:25][C:26](=[O:28])[CH3:27]>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH2:25][C:26](=[O:28])[CH3:27])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 132242-Methyl-8-hydroxyquinoline

생성물 1

HCID 107274142-Methyl-8-(2-oxopropoxy)quinoline수율 72%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-Methyl-8-hydroxyquinoline (0.80 g, 5 mmol), potassium carbonate (0.69 g, 5 mmol) and dry N,N-dimethylformamide (DMF) (40 ml) were stirred at room temperature for 30 min. To this solution was added chloroacetone (0.46 g, 5 mmol) in dry THF (10 ml) in one portion. The resulting mixture was stirred at room temperature for 24 h. (monitored by TLC) and then poured into ice water (100 ml). The pale yellow solid thus obtained was collected and crystallized from dichloromethane and ether to afford 2-methyl-8-(2-oxopropoxy)quinoline (10a) (0.77 g, 72%). mp: 99°-100° C.; 1H-NMR (CDCl3): δ2.35 (s, 3H, 2'-CH3), 2.79 (s, 3H, 2-CH3), 4.86 (s, 2H, OCH2), 6.88-7.44 (m, 3H, Ar--H), 7.33 (d, 1H, 3-H), 8.03 (d, 1H, 4-H).

후처리

  1. customThe pale yellow solid thus obtained
  2. customwas collected
  3. customcrystallized from dichloromethane and ether

출처 및 근거

ORD 기록
ord-f8fb5c390c78407f9107861dd3f4029d
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646164

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