ethyl 2-(ethoxycarbonyloxymethyl)-5-(4,5-di-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate → ethyl 5-(2-amino-4,5-dimethoxybenzoyl)-2-(ethoxycarbonyloxymethyl)-2H-1,2,3-triazole-4-carboxylate

HRID 841967Notes

Reaction equation

HRID 841967 reaction equation
[CH2:1]([O:3][C:4]([O:6][CH2:7][N:8]1[N:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([C:18](=[O:32])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:20]=2[N+:29]([O-])=O)=[N:9]1)=[O:5])[CH3:2].[H][H]>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[NH2:29][C:20]1[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:19]=1[C:18]([C:10]1[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:12][N:8]([CH2:7][O:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:9]=1)=[O:32]

Participants

5

Reactant 2

HCID 12051530ethyl 2-(ethoxycarbonyloxymethyl)-5-(4,5-di-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 12051531ethyl 5-(2-amino-4,5-dimethoxybenzoyl)-2-(ethoxycarbonyloxymethyl)-2H-1,2,3-triazole-4-carboxylateYield 95.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-(ethoxycarbonyloxymethyl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (45 mg) prepared in step (3a) was dissolved in ethyl acetate (1 ml). Palladium hydroxide (15 mg) was added to the solution. The mixture was stirred in a hydrogen atmosphere at room temperature for 15 hr. The reaction solution was filtered through Celite. The filtrate was concentrated under reduced pressure to give ethyl 5-(2-amino-4,5-dimethoxybenzoyl)-2-(ethoxycarbonyloxymethyl)-2H-1,2,3-triazole-4-carboxylate as a yellow oil (40 mg, 95%).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4499bcb9c5f946f1bd77c21842e3222b
Source dataset
uspto-grants-2002_04
Patent number
US06372735B1

Reaction notes

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