Water → Methyl 3-phenyl-1,2,4-triazolo[3,4-a]isoquinoline-6-carboxylate

HRID 2052803Notes

Reaction equation

HRID 2052803 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][N:3]=1.[C:16]([NH:24][NH2:25])(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[C:17]1([C:16]2[N:3]3[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]4[C:11]([C:2]3=[N:25][N:24]=2)=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11955BenzoylhydrazineHCID 3338790Methyl 1-chloroisoquinoline-4-carboxylate

Product 1

HCID 22136174Methyl 3-phenyl-1,2,4-triazolo[3,4-a]isoquinoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 1-chloroisoquinoline-4-carboxylate, prepared essentially according to procedures described in Example 1, part 4, (293 mg) and benzoic hydrazide (192 mg) in 8 ml of DMF is stirred at 100° C. overnight. The mixture is cooled and poured into water. The solid is then collected by filtration and dried to give the title compound as a solid (258 mg). LC-MS data for the title compound: HPLC: 2.34 min. MS (ES+) m/e 304 [M+H]+. (The HPLC retention time is obtained by the method of Example 1).

Workup

  1. customprepared essentially
  2. temperatureThe mixture is cooled
  3. filtrationThe solid is then collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-7efe4bd655724a2ba60c06de00faf032
Source dataset
uspto-grants-2008_02
Patent number
US07326709B2

Reaction notes

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