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

HRID 31093Notes

Reaction equation

HRID 31093 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-2c5fed0cab084379b2887f365ccd9e4f
Source dataset
uspto-grants-2008_09
Patent number
US07425556B2

Reaction notes

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