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

HRID 31093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31093
[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 10 minutes, 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 10 minutes
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. customThe solids were dried under high vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-2c5fed0cab084379b2887f365ccd9e4f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425556B2

Notizen zur Reaktion

Wird geladen…