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

HRID 263970

反応式

HRID 263970 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 107274142-Methyl-8-(2-oxopropoxy)quinoline収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f8fb5c390c78407f9107861dd3f4029d
出典データセット
uspto-grants-1997_07
特許番号
US05646164

関連ノート

読み込み中…