Trifluoroacetic acid → 1-Isoquinolinamine

HRID 1878641ノート

反応式

HRID 1878641 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 737421-Isoquinolinamine収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b7c55404060c487c868142749e1b6cb6
出典データセット
uspto-grants-2012_11
特許番号
US08314123B2

反応ノート

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