HCID 19934867, compound → 1-(2-Methylphenyl)triazolo[4,5-c]quinoline

HRID 37197Notes

Reaction equation

HRID 37197 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][CH:10]=2>O.Cl>[CH3:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:16]1[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=[N:1]1

Participants

5

Reactant 2

HCID 19934867HCID 19934867, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 102208231-(2-Methylphenyl)triazolo[4,5-c]quinolineYield 26.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (0.82 g, 12 mmol) in water (10 ml) was added dropwise to a stirred suspension of 3-amino-4-(2-methylphenylamino)quinoline (2.0 g,8 mmol) in 2M HCl (80 ml) at 0.5°. The solid gradually dissolved to give a pale orange solution which deposited a solid after about 1 hour. After warming to room temperature the solid was collected, washed with water and recrystallised from aqueous ethanol with charcoaling, to give the title compound as a white solid (0.55 g, 26%), m.p. 140°-142° .

Workup

  1. dissolutionThe solid gradually dissolved
  2. customto give a pale orange solution which
  3. customafter about 1 hour
  4. customwas collected
  5. washwashed with water
  6. customrecrystallised from aqueous ethanol with charcoaling

Sources & evidence

ORD record
ord-1ac80efc84324203a1ebd65da8db7ae6
Source dataset
uspto-grants-1995_05
Patent number
US05420135

Reaction notes

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