Hydrochloric Acid → 7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acid

HRID 1262408Notes

Reaction equation

HRID 1262408 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([C:18]#N)=[N:16]2)=[CH:11][CH:10]=1.[OH-:20].[Na+].Cl.[OH2:23]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([C:18]([OH:23])=[O:20])=[N:16]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water3×HCID 14798Sodium HydroxideHCID 667124197-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile

Product 1

HCID 667127107-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile (151 mg, 0.603 mmol) and 9.5 M of Sodium hydroxide in Water (0.20 mL, 1.9 mmol) were combined in Ethanol (6.0 mL) in a vial, which was then heated to reflux for 90 min. The mixture was removed from the heat and treated with 3.00 M of Hydrogen Chloride in Water (1.00 mL, 3.0 mmol), generating a precipitate, which was diluted with water (2 mL), stirred vigorously (thick suspension) then collected by filtration, washing with water (2×8 mL) and drying on the Buchner then in vacuo to afford 7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acid (145 mg, 89%). LCMS (HPLC): 0.76 min, m/z=270 (M+H); 1H-NMR (DMSO-d6): 13.55 (br s, 1H), 9.27 (s, 1H), 7.73 (d, 1H, J=7.5 Hz), 7.49 (m, 1H), 7.39 (d, 1H, J=4.6 Hz), 7.25 (s, 1H), 7.23 (d, 1H, J=4.6 Hz), 7.12 (m, 1H), 3.81 (s, 3H).

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for 90 min
  3. customThe mixture was removed from the
  4. temperatureheat
  5. filtrationthen collected by filtration
  6. washwashing with water (2×8 mL)
  7. customdrying on the Buchner

Sources & evidence

ORD record
ord-ce912842ba7948e188b2937c401545f7
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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