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Acetic Acid → methyl 6-(2,3-dihydro-1H-inden-2-ylamino)-2-methyl-4-phenylquinoline-3-carboxylate

HRID 570383
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 570383
CC(O)=O.[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:16])[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][C:28]1=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH:28]1[NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:16])[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]2[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
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Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 119832-IndanoneHCID 5049666Sodium triacetoxyborohydrideHCID 68293887Methyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylate

Produkt 1

HCID 68294847methyl 6-(2,3-dihydro-1H-inden-2-ylamino)-2-methyl-4-phenylquinoline-3-carboxylateAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A method of Abdel-Magid et al (J. Org. Chem., 61, 3849, 1996) was used: Glacial AcOH (0.2 ml) was added to a solution of the product of Step 2 (0.91 g, 3.31 mmol), 1H-inden-2(3H)-one (0.41 g, 3.31 mmol) and NaBH(OAc)3 (1.05 g, 4.9 mmol) in anhydrous 1,2-dichloroethane (12.5 ml). The resulting mixture was stirred overnight at room temperature under N2 than quenched by addition of 1N NaOH aq (1 ml). This was diluted to 60 ml with Et2O and washed with N2. The organic phase was dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (SiO2, CH2Cl2) to give pure product as a yellow solid (0.98 g, 72%). 1H NMR (300 MHz, CDCl3) δ 7.84 (d, J=9.0 Hz, 1H), 7.34-7.49(m, 5H), 7.15-7.18(m, 4H), 7.07(dd, J=1.7, 9.0 Hz, 1H), 6.49(d, J=1.7 Hz, 1H), 4.11-4.18(m, 2H), 3.55(s, 3H), 3.2(dd, J=6.2, 16 Hz, 2H), 2.8(dd, J=6.2, 16 Hz, 2H), 2.68(s, 3H).

Aufarbeitung

  1. customthan quenched by addition of 1N NaOH aq (1 ml)
  2. additionThis was diluted to 60 ml with Et2O
  3. washwashed with N2
  4. dry with materialThe organic phase was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customfiltrate evaporated to dryness under reduced pressure
  7. customThe residue was purified by flash column chromatography (SiO2, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-445724af04a74dabb370ba3c8395e1f8
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09023848B2

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