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Acetic Acid → 6-Amino-4-[(3-bromophenyl)amino]-8-dimethylaminomethyl-3-quinolinecarbonitrile

HRID 612059
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 612059
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([CH2:22][N:23]([CH3:25])[CH3:24])[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:26]#[N:27])[CH:5]=[CH:6][CH:7]=1.C(O)(=O)C>[Fe].CO>[NH2:19][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([CH2:22][N:23]([CH3:24])[CH3:25])[CH:15]=1)[N:12]=[CH:11][C:10]([C:26]#[N:27])=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1
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Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 102026834-[(3-Bromophenyl)amino]-8-dimethylaminomethyl-6-nitro-3-quinolinecarbonitrile

Produkt 1

HCID 101353526-Amino-4-[(3-bromophenyl)amino]-8-dimethylaminomethyl-3-quinolinecarbonitrileAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 887Methanol
Lösungsmittel

Versuchsvorschrift

A stirred mixture of 4-[(3-bromophenyl)amino]-8-dimethylaminomethyl-6-nitro-3-quinolinecarbonitrile (5.98 g, 14.1 mmol), iron powder (2.76 g, 49 mg-atoms), acetic acid (5.67 ml, 99 mmol), and 70 ml of methanol was refluxed for 2 h and then evaporated to remove methanol. The residue was stirred with water for 10 m, and the orange solid was filtered off and washed with 2% acetic acid. The total filtrate was basified to pH 10 with 5 N sodium hydroxide. The resulting precipitate was extracted with methylene chloride. The extract was washed with water, dried, and concentrated. The residue was subjected to chromatography on silica gel with ethyl acetate-methanol-triethylamine to give 3.34 g of amber solid; mass spectrum (electrospray, m/e) M+H 396.2, 398.1.

Aufarbeitung

  1. temperaturewas refluxed for 2 h
  2. customevaporated
  3. customto remove methanol
  4. filtrationthe orange solid was filtered off
  5. washwashed with 2% acetic acid
  6. extractionThe resulting precipitate was extracted with methylene chloride
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c731892fb7d1496eaae24f6087bf7afb
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06002008

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