Citric Acid → HCID 178515799, compound

HRID 1017630Notes

Reaction equation

HRID 1017630 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][C:14](Cl)=[CH:15][CH:16]=[C:11]2[N:10]=[N:9]1.FC1C=CC=CC=1N.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:31]>CS(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][C:14]([OH:31])=[CH:15][CH:16]=[C:11]2[N:10]=[N:9]1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 95842-FluoroanilineHCID 14798Sodium HydroxideHCID 12445505HCID 12445505, compound

Product 1

HCID 178515799HCID 178515799, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-(2-fluorophenyl)-5-chloro-1,2,3-triazolo[4,5-b]pyridine (1.01 g, 4.06 mmol; prepared following the procedure described in GB Patent No. 1268772 but using 2-fluoroaniline instead of aniline) and 2M sodium hydroxide (4 ml) in DMSO (15 ml) was stirred at 100° C. under nitrogen for 3 h. The mixture was cooled, diluted with water (250 ml) and neutralised with aqueous citric acid. After standing for 18 h, the brown precipitate was collected, dissolved in dichloromethane (100 ml), dried (Na2SO4), filtered and concentrated to give 3-(2-fluorophenyl)-5-hydroxy-1,2,3-triazolo[4,5-b]pyridine (0.80 g, 86%) as a brown solid. δH (360 MHz; d6-DMSO) 6.81 (1H, broad d, J=9), 7.50 (1H, dd, J=8 and 8), 7.60 (1H, dd, J=8 and 7), 7.68-7.72 (1H, m), 7.81 (1H, ddd, J=8, 8 and 2), 8.44 (1H, broad d, J=9) and 12.15 (1H, broad s); m/z (ES+) 231 (M+H+).

Workup

  1. customprepared
  2. temperatureThe mixture was cooled
  3. waitAfter standing for 18 h
  4. customthe brown precipitate was collected
  5. dissolutiondissolved in dichloromethane (100 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3fc0b19fc82244b3a4127a16d6f66d7d
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

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