Hydrochloric Acid → 2-formyl-1H-indole-3-carbonitrile

HRID 2097100노트

반응식

HRID 2097100 반응식
Cl.C(OC(OCC)[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]#[N:16])=[C:7]1[CH:17]=[O:18])C.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH:17]([C:7]1[NH:6][C:14]2[C:9]([C:8]=1[C:15]#[N:16])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:18]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 592776141-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile

생성물 1

HCID 592775632-formyl-1H-indole-3-carbonitrile수율 84.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

Hydrochloric acid (4 mL, 20%) was added to a THF (100 mL) solution of 1-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile (5.33 g, 19.57 mmol) at 0° C. The mixture was stirred at 20° C. for 41 h then treated with 5% aqueous K2CO3 (25 mL). The reaction mixture was concentrated to 50 mL and treated with methylene chloride (200 mL). The organic layer was washed with water, dried and evaporated to afford the title compound (2.81 g, 84%). 1H NMR (300 MHz, DMSO-d6, δ): 13.20 (s, br, 1H), 10.02 (s, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.63 (d, J=7.7 Hz, 1H), 7.51 (t, J=7.1 Hz, 1H), 7.37 (t, J=7.5 Hz, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated to 50 mL
  2. additiontreated with methylene chloride (200 mL)
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-4a47460586bb4ca99254f411992ea733
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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