Acridone → 10-(3-(tetrahydro-2H-pyran-2-yloxy)-1-propyl)acridin-9-one

HRID 482234

反応式

HRID 482234 の反応式
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1>CN(C)C=O>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[O:22][CH2:21][CH2:20][CH2:19][N:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:13](=[O:15])[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2

参加物

5

反応物 3

HCID 2015AcridoneHCID 24758Sodium hydrideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

生成物 1

HCID 1879931210-(3-(tetrahydro-2H-pyran-2-yloxy)-1-propyl)acridin-9-one収率 33%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of acridone (15 g, 0.077 mol) in dry dimethylformamide (200 ml), sodium hydride (3.7 g, 0.092 mol, 60% dispersion in mineral oil) was added in 4 portions under an atmosphere of nitrogen. The reaction mixture was stirred until gas evolution had ceased. A solution of 2-(3-bromo-1-propyloxy)tetrahydro-2H-pyran (21.7 g, 0.092 mol) in dry dimethylformamide (100 ml) was added dropwise. The reaction mixture was heated to 80° C. for 4 h and stirred overnight at room temperature. The reaction mixture was poured onto ice water (800 ml) and extracted with ethyl acetate (4×200 ml). The combined ethyl acetate extracts were washed with water (3×300 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was dissolved in diethyl ether (150 ml) and unchanged starting material was filtered off. The solvent was evaporated in vacuo and the residue was crystallised from 96% ethanol (150 ml), filtered and washed with ethanol (96%, 30 ml) and diethyl ether (50 ml). This procedure was repeated twice, yielding 8.5 g (33%) of 10-(3-(tetrahydro-2H-pyran-2-yloxy)-1-propyl)acridin-9-one as yellowish crystals. M.p. 140.5°-141.5° C.

後処理

  1. stirringstirred overnight at room temperature
  2. additionThe reaction mixture was poured onto ice water (800 ml)
  3. extractionextracted with ethyl acetate (4×200 ml)
  4. washThe combined ethyl acetate extracts were washed with water (3×300 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. dissolutionThe residue was dissolved in diethyl ether (150 ml)
  9. filtrationwas filtered off
  10. customThe solvent was evaporated in vacuo
  11. customthe residue was crystallised from 96% ethanol (150 ml)
  12. filtrationfiltered
  13. washwashed with ethanol (96%, 30 ml) and diethyl ether (50 ml)

出典と根拠

ORDレコード
ord-b25a4c4cfdd044bd8b22e4c46a6f4639
出典データセット
uspto-grants-1998_08
特許番号
US05795888

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