Water → HCID 18409092、化合物

HRID 1195162ノート

反応式

HRID 1195162 の反応式
[CH3:1][N:2](OCC1C=CC=CC=1)[C:3]1([CH3:21])[CH2:12][CH2:11][CH2:10][C:9]2[N:8]=[C:7]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:6]=[CH:5][C:4]1=2.B.O1CCCC1.O>O1CCCC1>[CH3:1][NH:2][C:3]1([CH3:21])[CH2:12][CH2:11][CH2:10][C:9]2[N:8]=[C:7]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:6]=[CH:5][C:4]1=2

参加物

5

反応物 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 19026196HCID 19026196、化合物

生成物 1

HCID 18409092HCID 18409092、化合物収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

5,6,7,8-Tetrahydro-N,5-dimethyl-N,2-bis(phenylmethoxy)-5-quinolinamine (12.3 g) in tetrahydrofuran (160 ml) at 0° C. was treated dropwise with borane-tetrahydrofuran complex (1M in tetrahydrofuran, 63.4 ml). The solution was heated under reflux for 3 hrs, cooled to 0° C., and water (30 ml) was added. The reaction mixture was concentrated in vacuo, 20% potassium hydroxide solution (60 ml) was added, and the mixture was heated at reflux for 2 hrs. The mixture was cooled, acidified with conc hydrochloric acid, and washed with diethyl ether. The aqueous phase was basified with 20% potassium hydroxide solution and extracted with dichloromethane. The combined organic layers were washed with brine, dried over potassium carbonate, filtered, and the filtrate was concentrated to afford 6.3 g (92%) of product.

後処理

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 3 hrs
  3. concentrationThe reaction mixture was concentrated in vacuo, 20% potassium hydroxide solution (60 ml)
  4. additionwas added
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 2 hrs
  7. temperatureThe mixture was cooled
  8. washwashed with diethyl ether
  9. extractionextracted with dichloromethane
  10. washThe combined organic layers were washed with brine
  11. dry with materialdried over potassium carbonate
  12. filtrationfiltered
  13. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-2432a3b5140143afadf0ee858e7a20c5
出典データセット
uspto-grants-1992_05
特許番号
US05110815

反応ノート

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