HCID 18937721, compound → HCID 18937609, compound

HRID 357643Notes

Reaction equation

HRID 357643 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18](=[O:28])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-])=O)[N:10]=[N:9]2)=[CH:5][CH:4]=1>C(O)C.[Pd]>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([C:11]1[N:10]=[N:9][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:30][CH:29]=2)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:28]

Participants

4

Reactant 1

HCID 18937721HCID 18937721, compound

Product 1

HCID 18937609HCID 18937609, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

Ethyl 1-(4-methoxybenzyl)-4-(2-nitrobenzoyl)-1,2, 3-triazole-5-carboxylate (629 mg, 1.53 mmole) was dissolved in ethanol (6.0 ml), and 10% palladium on carbon (58 mg) was added. After the mixture was stirred under a hydrogen atmosphere at room temperature for 16 hours, 10% palladium on carbon (60 mg) was added, and the mixture was further stirred for 2 hours. The reaction mixture was filtered through celite, and the solvent was removed under reduced pressure. Precipitate was collected by filtration to give ethyl 4-(2-aminobenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate (548 mg, 94.2%) as a yellow crystalline powder.

Workup

  1. stirringthe mixture was further stirred for 2 hours
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe solvent was removed under reduced pressure
  4. filtrationPrecipitate was collected by filtration

Sources & evidence

ORD record
ord-3c5ec31b2db44b2db6ba5013261355bf
Source dataset
uspto-grants-1998_11
Patent number
US05840895

Reaction notes

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