Hydrochloric Acid → 7-Methoxyisoquinoline

HRID 1008547

반응식

HRID 1008547 반응식
CO[CH:3](OC)[CH2:4][NH2:5].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC.Cl>C1(C)C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:15]([CH:3]=[CH:4][N:5]=[CH:13]2)=[CH:16][CH:17]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 115693-MethoxybenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetal

생성물 1

HCID 5943757-Methoxyisoquinoline수율 84%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
5 °C

실험 절차

Aminoacetaldehyde dimethyl acetal (81.9 mL) was added to a solution of 60.8 mL of 3-methoxy-benzaldehyde in 600 mL of toluene. The mixture was refluxed for 5 h using a Dean-Stark trap and subsequently cooled to 5° C. In a nitrogene atmosphere trifluoroacetic acid anhydride (209 mL) and borontrifluoride etherate (185 mL) were added in succession at such a rate, that the internal temperature was kept below 10° C. After stirring for 3 days at room temperature the the reaction mixture was poured on ice, 250 mL 2 N hydrochloric acid added and the organic layer extracted with 1 N hydrochloric acid. The pH value of the combined aqueous extracts was adjusted to pH 9 by adding concentrated aqueous ammonia. Extraction with ethyl acetate, followed by drying and removal of the solvent in vacuo gave 66.9 g (84%) of the title compound as a light brownish oil. EI-MS: 159 (M+).

후처리

  1. temperatureThe mixture was refluxed for 5 h
  2. customwas kept below 10° C
  3. additionadded
  4. extractionthe organic layer extracted with 1 N hydrochloric acid
  5. additionby adding concentrated aqueous ammonia
  6. extractionExtraction with ethyl acetate
  7. customby drying
  8. customremoval of the solvent in vacuo

출처 및 근거

ORD 기록
ord-6676c3845f2e4c16aaac28494505eb45
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06797710B2

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