Trimethyl orthoacetate → 8-Iodo-1-methyl-5-phenyl-[1,2,4]triazolo[4,3-a]quinoline

HRID 2075698Notes

Reaction equation

HRID 2075698 reaction equation
[I:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:8]([NH:12][NH2:13])=[N:9]2)=[CH:4][CH:3]=1.[C:20](OC)(OC)(OC)[CH3:21]>CCO>[I:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:8]3[N:9]2[C:20]([CH3:21])=[N:13][N:12]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 67090996HCID 67090996, compound

Product 1

HCID 670910128-Iodo-1-methyl-5-phenyl-[1,2,4]triazolo[4,3-a]quinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To (7-Iodo-4-phenyl-quinolin-2-yl)-hydrazine (400 mg, 1.1 mmol) in EtOH (5 mL) was added trimethyl orthoacetate (2 mL), and the reaction was heated to 80° C. overnight. After cooling to room temperature, the mixture was concentrated and purified by silica gel chromatography (40-100% EtOAc in hexanes) to give the desired product, 5u.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. custompurified by silica gel chromatography (40-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b08166077181491a88a1f5d236b5e3ea
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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