Ethylamine → 2-(Ethylamino)-6-methoxyquinoline-3-carbaldehyde

HRID 1620204노트

반응식

HRID 1620204 반응식
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[CH2:16]([NH2:18])[CH3:17]>C1COCC1>[CH2:16]([NH:18][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1)[CH3:17]

참가 물질

4

반응물 2

HCID 6341EthylamineHCID 6890792-Chloro-6-methoxyquinoline-3-carbaldehyde

생성물 1

HCID 866698182-(Ethylamino)-6-methoxyquinoline-3-carbaldehyde수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
160 °C

실험 절차

To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.51 g, 6.80 mmol) in THF (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added ethylamine (2 M in THF, 33.8 mL, 67.6 mmol) and the mixture was stirred at 160° C. for 6 h under microwave irradiation. After cooling to RT, the volatiles were removed under vacuum at 40° C. and the resulting yellow oil was taken up in a mixture of THF:1 N aq. HCl=1:1 (50 mL) and stirred for 15 min at RT. THF was removed at 40° C. under vacuum and the residue was then neutralised with a saturated NaHCO3 aqueous solution before to be extracted with CH2Cl2 (100 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and concentrated at 40° C. under vacuum to give 2-(ethylamino)-6-methoxyquinoline-3-carbaldehyde SLA 28162 as an orange oil (1.19 g, 76% yield).

후처리

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed under vacuum at 40° C.
  3. additionthe resulting yellow oil was taken up in a mixture of THF
  4. stirring1 N aq. HCl=1:1 (50 mL) and stirred for 15 min at RT
  5. customTHF was removed at 40° C. under vacuum
  6. extractionto be extracted with CH2Cl2 (100 mL)
  7. washThe organic phase was washed with brine (20 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated at 40° C. under vacuum

출처 및 근거

ORD 기록
ord-9646a70b5ce7485ca8e04d2a2db01c29
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772316B2

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