Ammonia → Quinoxaline-6-carboxamide

HRID 1593365Notes

Reaction equation

HRID 1593365 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13]C)=O)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.[NH3:15]>CO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH2:15])=[O:13])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2781239Methyl 6-quinoxalinecarboxylate

Product 1

HCID 11240756Quinoxaline-6-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of methyl quinoxaline-6-carboxylate (2.00 g) in methanol (7.0 mL) and 28-30% ammonia (14 mL) was stirred in a sealed tube at room temperature for 16 h. The precipitated solid was filtered, washed with water and dried under high vacuum to give quinoxaline-6-carboxamide as a white powder. A portion of this material (0.10 g) was suspended in anhydrous dichloromethane and treated with oxalyl chloride (1.0 mL of a 2M solution in dichloromethane) under a nitrogen atmosphere. The mixture was heated at reflux for 16 h and concentrated under reduced pressure. The residue was dissolved in anhydrous tetrahydrofuran (1 mL) and added to an ice-cooled solution of 3-aminobiphenyl (0.98 g) in anhydrous tetrahydrofuran (1 mL). The mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue taken up in methanol and filtered to give N-{[(3-phenylphenyl)-amino]carbonyl}quinoxalin-6-ylcarboxamide as a white powder. 1H NMR (DMSO-d6) δ 7.37-7.47 (m, 3H), 7.50 (t, J=7.2 Hz, 2H), 7.65 (d, J=7.8 Hz, 1H), 7.69 (d, J=7.2 Hz, 2H) 7.91 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 8.37 (dd, J=8.8, 1.9 Hz, 1H), 8.84 (d, J=1.9 Hz, 1H), 9.09 (s, 2H), 10.85 (s, 1H), 11.44 (s, 1H). MS (ES) m/z 369.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-eabae38a225f49efaa18a519236d6c06
Source dataset
uspto-grants-2007_11
Patent number
US07297696B2

Reaction notes

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