Water → HCID 18409092, 화합물

HRID 1586985노트

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HRID 1586985 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 19026196HCID 19026196, 화합물

생성물 1

HCID 18409092HCID 18409092, 화합물수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9b2bc3a09aff49bdb72131e4da56e825
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05216164

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