Dichloromethane methanol → Methyl 5-aminoisoquinoline-3-carboxylate

HRID 1791303

반응식

HRID 1791303 반응식
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:14]([O:16][CH3:17])=[O:15])[N:8]=[CH:9]2)([O-])=O.CO.C(Cl)Cl>C(O)(=O)C.O.[Fe]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:14]([O:16][CH3:17])=[O:15])[N:8]=[CH:9]2

참가 물질

5

반응물 2

HCID 21226129Dichloromethane methanolHCID 22032663Methyl 5-nitroisoquinoline-3-carboxylate

생성물 1

HCID 22032628Methyl 5-aminoisoquinoline-3-carboxylate

시약·촉매·용매 2

HCID 23925Iron촉매HCID 21899381Acetic acid--water (1/1)용매

실험 절차

The product of Example 71A (10.33 g, 44.5 mmol) in acetic acid/water (3/1) (320 mL) was treated with iron powder (5.06 g, 90.7 mmol). After stirring for 16 hours at room temperature, the reaction mixture was filtered the filtrate concentrated under reduced pressure to approximately half the original volume. The mixture was then extracted with dichloromethane (3×200 mL). The organic fractions were combined, dried (MgSO4), and the filtrate concentrated under reduced pressure to afford crude material. A precipitate formed in the aqueous phase after sitting for several hours. This was filtered to afford additional crude material. The crude material was purfidied by column chromatography (2% methanol/CH2Cl2) to provide the title compound. MS (ESI+) m/z 203 (M+H)+; MS (ESI−) m/z 201 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 3.92 (s, 3H), 6.34 (s, 2H), 6.96 (dd, J 1.0, 7.8, 1H), 7.31 (d, J 8.1, 1H), 7.51 (t, J 7.9, 1H), 8.82 (s, 1H), 9.15 (s, 1H); Anal. Calcd for C11H10N2O2: C, 65.34; H, 4.99; N, 13.85. Found: C, 65.03; H, 4.95; N, 13.65.

후처리

  1. filtrationthe reaction mixture was filtered the filtrate
  2. concentrationconcentrated under reduced pressure to approximately half the original volume
  3. extractionThe mixture was then extracted with dichloromethane (3×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto afford crude material
  7. customA precipitate formed in the aqueous phase
  8. waitafter sitting for several hours
  9. filtrationThis was filtered
  10. customto afford additional crude material

출처 및 근거

ORD 기록
ord-01fb787146f347a1af791d906562fe79
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074805B2

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