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Acetic Acid → 4-(4-Hydroxymethyl-2-methylanilino)-6,7-dimethoxy-3-quinolinecarboxamide

HRID 1822857
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1822857
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][C:7]([C:15]([NH2:17])=[O:16])=[C:6]2[NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](OC)=[O:26])=[CH:21][C:20]=1[CH3:29].[BH4-].[Li+].O.C(O)(=O)C>O1CCCC1>[OH:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][C:7]=2[C:15]([NH2:17])=[O:16])=[C:20]([CH3:29])[CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic Acid2×HCID 962WaterHCID 4148881Lithium borohydride2×HCID 22170299HCID 22170299, Verbindung

Produkt 1

HCID 221702424-(4-Hydroxymethyl-2-methylanilino)-6,7-dimethoxy-3-quinolinecarboxamideAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

6,7-Dimethoxy-4-(4-methoxycarbonyl-2-methylanilino)-3-quinolinecarboxamide (0.080 g, 0.20 mmol) was dissolved in tetrahydrofuran (25 ml, dried over 4 A molecular sieves). Lithium borohydride (0.15 mg, 6.8 mmol) was added. The mixture was stirred for 24 h and additional lithium borohydride (0.050 g, 2.2 mmol) was added. The reaction mixture was stirred for additional 25 h and then poured into a cooled mixture of water (20 ml) and acetic acid (0.5 ml). Acetic acid (2 ml) was added and the mixture was evaporated under reduced pressure. The residue was suspended in water, filtered and the precipitate was washed with water and re-crystallized from aqueous methanol to give the title compound (32 mg, 43%).

Aufarbeitung

  1. customdried over 4 A molecular sieves)
  2. stirringThe reaction mixture was stirred for additional 25 h
  3. customthe mixture was evaporated under reduced pressure
  4. filtrationfiltered
  5. washthe precipitate was washed with water
  6. customre-crystallized from aqueous methanol

Quellen und Nachweise

ORD-Eintrag
ord-db4a0051cd6745c88018d5812e9fbb3b
Quelldatensatz
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07037925B2

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