Trifluoroacetic acid → 1-Isoquinolinamine

HRID 1878641노트

반응식

HRID 1878641 반응식
COC1C=CC(C[NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][N:10]=2)=CC=1.COC1C=CC(CNC2C3C(=CC=C(N(C)C)C=3)C=C(C3C=CC=C(OC)C=3)N=2)=CC=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 19771021HCID 19771021, 화합물HCID 69298933N1-(4-Methoxybenzyl)-3-(3-methoxyphenyl)-N7,N7-dimethylisoquinoline-1,7-diamine

생성물 1

HCID 737421-Isoquinolinamine수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A reaction mixture of N1-(4-methoxy benzyl)-isoquinolinamine compound III (300 mg, 0.73 mmol) and trifluoroacetic acid (5 mL) in methylene chloride (5 mL) was refluxed for 2 days. A solution of NaHCO3 was added and the reaction mixture was extracted with methylene chloride. The combined organic extracts were washed with water, dried, and concentrated. The residue was purified by column chromatography on silica gel with n-hexane-ethyl acetate (1:1) to afford 1-amino isoquinoline (151 mg, 71%). The 1-amino compound was dissolved in acetone (5 mL) and 5 drops of concentrated HCl was added. The hydrochloride salt was filtered and filter cake was washed with acetone. After drying, 120 mg of 1-amino isoquinoline hydrochloride was obtained (Compound 13, 50%). 1H NMR (300 MHz, DMSO-d6) δ: 13.57 (s, 1H), 9.37 (s, 2H), 7.79 (d, 1H), 7.55-7.39 (m, 6H), 7.02 (m, 1H), 3.87 (s, 3H), 3.06 (s, 6H).

후처리

  1. temperaturewas refluxed for 2 days
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel with n-hexane-ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-b7c55404060c487c868142749e1b6cb6
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314123B2

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