Ammonium Hydroxide → 7-Methoxy-2,6-dimethylquinoline

HRID 338950

반응식

HRID 338950 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[CH3:10])[NH2:6].[CH:11](=O)/[CH:12]=[CH:13]/[CH3:14].[NH4+].[OH-]>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:7]([CH:11]=[CH:12][C:13]([CH3:14])=[N:6]2)=[CH:8][C:9]=1[CH3:10]

참가 물질

5

반응물 3

HCID 14923Ammonium HydroxideHCID 278823-Methoxy-4-methylanilineHCID 447466Crotonaldehyde

생성물 1

HCID 867074717-Methoxy-2,6-dimethylquinoline수율 42.5%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

To 3-methoxy-4-methylaniline (1.0 g, 7.29 mmol) in refluxing in 6N HCl (50 mL) was added dropwise (E)-but-2-enal (1.02 g, 14.6 mmol). The reaction was heated to reflux for 2 hours then cooled down and neutralized with NH4OH. The organic phase was extracted with DCM and the combined organic phases dried over MgSO4, filtered and concentrated under reduced pressure to leave a dark residue. The residue was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 7-methoxy-2,6-dimethylquinoline (580 mg, 29.7% yield) as a beige solid.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethen cooled down
  4. extractionThe organic phase was extracted with DCM
  5. dry with materialthe combined organic phases dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave a dark residue
  9. customThe residue was purified by reverse phase chromatography (SP4, 25M
  10. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

출처 및 근거

ORD 기록
ord-d1a62e775ff14853b31c0c1618bab9fe
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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