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Acetic Acid → Methyl 2-{2-[(4-methoxyphenyl)amino]ethyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616153
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Reaktionsgleichung

Reaktionsgleichung von HRID 1616153
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:5]=[CH:4][N:3]1[CH2:16][CH:17]=O.[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][CH2:17][CH2:16][N:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=3)[C:2]2=[O:1])=[CH:23][CH:22]=1
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Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7732P-AnisidineHCID 5003444Sodium cyanoborohydrideHCID 86664205Methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate

Produkt 1

HCID 67282872Methyl 2-{2-[(4-methoxyphenyl)amino]ethyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate (0.10 g, 0.41 mmol) and 4-methoxyaniline (65 mg, 0.53 mmol) in methanol (2 mL) was stirred at rt for 30 mins. Then acetic acid (2.3 μL, 0.04 mmol) and sodium cyanoborohydride (64 mg, 1.0 mmol) was added and the reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (20% to 70% EtOAc/hexanes) to afford methyl 2-{2-[(4-methoxyphenyl)amino]ethyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.12 g, 83%). LC-MS: (FA) ES+ 353.

Aufarbeitung

  1. extractionextracted with DCM (2×)
  2. washThe combined organic phases were then washed with water, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash silica gel chromatography (20% to 70% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-af57a4746c3946ecabb98b0a0c0956c1
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765773B2

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