Hydrochloric Acid → 6-Methoxy-1H-indole-3-carboxaldehyde

HRID 1976722

반응식

HRID 1976722 반응식
O=P(Cl)(Cl)Cl.[CH3:6][O:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][NH:14]2)=[CH:10][CH:9]=1.[OH-].[K+].Cl.CN([CH:23]=[O:24])C>O>[CH3:6][O:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH:23]=[O:24])=[CH:13][NH:14]2)=[CH:10][CH:9]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 766596-Methoxy-1H-indole

생성물 1

HCID 9072146-Methoxy-1H-indole-3-carboxaldehyde수율 69%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
5 °C

실험 절차

A mixture of DMF (7 mL, 90 mm) and POCl3 (2.25 mL, 24.5 mmol) which had been cooled to 5° C., was treated with known 6-methoxy-1H-indole. After stirring at room temperature for 1 hour, the mixture was heated at 45° C. for 1 hour, then allowed to cool to room temperature overnight. The reaction mixture was poured into ice (100 mL), and stirred for 30 minutes at which time a solution of KOH (9.6 g, 171 mm) in H2O (20 mL) was added dropwise. After stirring for 30 minutes, then heating for 1 hour at 60° C., the reaction was cooled to 30° C., and the pH adjusted to 7 with 1N HCl. The mixture was extracted with EtOAc(50 mL×3), the organic fractions were combined, dried over MgSO4, filtered and evaporated. The residue was purified by crystallization from methanol to afford 6-methoxy-1H-indole-3-carboxaldehyde (1.65 g, 69%).

후처리

  1. temperaturethe mixture was heated at 45° C. for 1 hour
  2. temperatureto cool to room temperature overnight
  3. additionwas added dropwise
  4. stirringAfter stirring for 30 minutes
  5. temperatureheating for 1 hour at 60° C.
  6. temperaturethe reaction was cooled to 30° C.
  7. extractionThe mixture was extracted with EtOAc(50 mL×3)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by crystallization from methanol

출처 및 근거

ORD 기록
ord-5c4db0a1b92543749ca98c104f1e7f5d
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06228877B1

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