6-Quinoxalinamine → 6-Quinoxalinamine,2-methyl-(9CI)

HRID 1941133Notes

Reaction equation

HRID 1941133 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=2)[N:3]=1.NC1C=C2C(=CC=1)N=CC=N2>CO>[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:12])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 2378596-QuinoxalinamineHCID 824610HCID 824610, compound

Product 1

HCID 126667146-Quinoxalinamine,2-methyl-(9CI)Yield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A thick-walled Parr hydrogenation flask was charged with 2-methyl-6-nitroquinoxaline (10.0 g, 52.9) and CH3OH (200 ml). The flask was flushed with a stream of nitrogen and 10% by weight palladium on charcoal (500 mg) was added. The flask was pressurized with hydrogen to 50 psi and maintained at this pressure for three (3) hours. The reaction mixture was filtered and washed through silicon dioxide and concentrated in vacuo to yield a tan solid. The crude material was chromatographed (SiO2 ; 95/5 CHCl3 /CH3OH saturated with NH3 (g)) and recrystallized from benzene to yield 7.4 g (a yield of 88%) of a tan solid. Using various analytical procedures, this tan solid was determined to be 2-methyl-,6-aminoquinoxaline.

Workup

  1. customThe flask was flushed with a stream of nitrogen and 10% by weight palladium on charcoal (500 mg)
  2. additionwas added
  3. temperaturemaintained at this pressure for three (3) hours
  4. filtrationThe reaction mixture was filtered
  5. washwashed through silicon dioxide
  6. concentrationconcentrated in vacuo
  7. customto yield a tan solid
  8. customThe crude material was chromatographed (SiO2 ; 95/5 CHCl3 /CH3OH saturated with NH3 (g))
  9. customrecrystallized from benzene
  10. customto yield 7.4 g (a yield of 88%) of a tan solid

Sources & evidence

ORD record
ord-fe98348a72114cbc8788685ba21879fc
Source dataset
uspto-grants-1997_12
Patent number
US05703077

Reaction notes

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