Citric Acid → 8-Phenyl-2,3-dihydropyrrolo[1,2-d][1,2,4]triazine-1,4-dione

HRID 1478400Notes

Reaction equation

HRID 1478400 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][NH:9][C:8]=2[C:12]([NH:14][NH:15][C:16]([O:18]C)=O)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O>[C:1]1([C:7]2[CH:11]=[CH:10][N:9]3[C:8]=2[C:12](=[O:13])[NH:14][NH:15][C:16]3=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 90424200methyl 2-(3-phenyl-1H-pyrrole-2-carbonyl)hydrazinecarboxylate

Product 1

HCID 904249208-Phenyl-2,3-dihydropyrrolo[1,2-d][1,2,4]triazine-1,4-dioneYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 2-(3-phenyl-1H-pyrrole-2-carbonyl)hydrazinecarboxylate (4.00 g, 15.0 mmol) in ethanol (60 mL) was added potassium hydroxide (4.33 g, 770 mmol) at room temperature and heated to 85° C. for 30 min. The reaction mixture was evaporated under reduced pressure to give a brown solid, which was redissolved in water (100 mL) and acidified with saturated citric acid solution to pH 7. The solid obtained was filtered through the Buchner funnel and further it was triturated with hexane to yield 8-phenyl-2,3-dihydropyrrolo[1,2-d][1,2,4]triazine-1,4-dione (3.00 g, 86.0%) as a white solid. LCMS method B-3: retention time 1.59 min, [M+1]=228.0. 1H NMR (400 MHz, DMSO-d6) δ ppm: 6.88 (d, J=2.8 Hz, 1H), 7.29-7.39 (m, 3H), 7.64-7.66 (m, 2H), 7.76 (d, J=2.8 Hz, 1H), 11.43 (br s, 2H).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto give a brown solid, which
  3. customThe solid obtained
  4. filtrationwas filtered through the Buchner funnel and further it
  5. customwas triturated with hexane

Sources & evidence

ORD record
ord-4103865d4a6d4898b4ca94f3ee7daf5f
Source dataset
uspto-grants-2016_08
Patent number
US09403834B2

Reaction notes

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