Hydrochloric Acid → 4-Amino-8-bromo-N-methyl-cinnoline-3-carboxamide hydrochloric acid salt

HRID 2375586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375586
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][N:9]=[C:10]([C:15]#[N:16])[C:11]([NH:13][CH3:14])=[O:12].[Cl-:17].[Al+3].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[ClH:17].[NH2:16][C:15]1[C:4]2[C:3](=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)[N:8]=[N:9][C:10]=1[C:11]([NH:13][CH3:14])=[O:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 866130992-[(2-bromophenyl)-hydrazono]-N-methyl-2-cyanoacetamide

Produkt 1

HCID 672290504-Amino-8-bromo-N-methyl-cinnoline-3-carboxamide hydrochloric acid saltAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 250 mL round-bottomed flask was charged with 2-[(2-bromophenyl)-hydrazono]-N-methyl-2-cyanoacetamide (2.00 g, 7.12 mmol), aluminum chloride (3.46 g, 25.97 mmol), and anhydrous toluene (68 mL). The reaction was gently refluxed for 45 minutes, cooled to room temperature, and slowly treated with 2N HCl (68 mL). A precipitate formed. The mixture was heated to 90° C. for 10minutes, cooled to room temperature, and filtered. The solids were dried under high vacuum at 50° C. to afford the title compound (2.02 g, 90%). 1H NMR (300.132 MHz, DMSO) δ 9.08 (d, J=4.7 Hz, 1H), 8.56 (dd, J=8.4, 0.8 Hz, 1H), 8.28 (dd, J=7.6, 0.7 Hz, 1H), 7.65 (t, J=8.0 Hz, 1H), 2.89 (d, J=4.7 Hz, 3H). MS APCI, m/z=281/283 (M+H). HPLC 1.61 min.

Aufarbeitung

  1. temperatureThe reaction was gently refluxed for 45 minutes
  2. customA precipitate formed
  3. temperatureThe mixture was heated to 90° C. for 10minutes
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. customThe solids were dried under high vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-308432ce33e44e858e24338d811c7a9f
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465795B2

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