1,4-Dioxane → HCID 135515429, compound

HRID 2086579Notes

Reaction equation

HRID 2086579 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[O:19]1[CH2:24][CH2:23]OCC1>[Ni]>[CH2:12]([NH:11][C:4]1[N:3]=[C:2]2[C:7](=[CH:6][CH:5]=1)[N:8]=[CH:17][C:18]([C:13]1[CH:12]=[CH:23][C:24]([OH:19])=[CH:15][CH:14]=1)=[N:1]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 10354455HCID 10354455, compound

Product 1

HCID 135515429HCID 135515429, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

2-Amino-6-benzylamino-3-nitropyridine (25 g, 0.10 mol) was hydrogenated under 5.5 bar of H2 in the presence of 10 g of Raney-Ni in 400 mL of dioxane at 60 C. After 2 hours the reaction mixture was cooled to room temperature, filtrated and 4-hydroxy phenylglyoxal was added and stirred for 2 hours under an argon atmosphere. The suspension was then diluted with water, the solid was collected by filtration, washed with water, recrystallized from 2-propanol, and dried at 50 C in vacuo to give 6-benzylamino-3-(4-hydroxyphenyl)-5-azaquinoxaline (8 g, 24.4%, m.p. 271-273 C).

Workup

  1. filtrationfiltrated
  2. addition4-hydroxy phenylglyoxal was added
  3. additionThe suspension was then diluted with water
  4. filtrationthe solid was collected by filtration
  5. washwashed with water
  6. customrecrystallized from 2-propanol
  7. customdried at 50 C in vacuo

Sources & evidence

ORD record
ord-f2a9216349a24d0db5a7e39eb1dce111
Source dataset
uspto-grants-2004_04
Patent number
US06727252B1

Reaction notes

Loading…