t-butyl N-[5-(4-hydroxy-2,5-dimethylphenoxy)-2-nitrophenyl]-N-methylcarbamate → t-Butyl N-[2-amino-5-(4-hydroxy-2,5-dimethylphenoxy)phenyl]-N-methylcarbamate

HRID 2303893Notes

Reaction equation

HRID 2303893 reaction equation
[OH:1][C:2]1[C:26]([CH3:27])=[CH:25][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N+:22]([O-])=O)=[C:11]([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:12]=2)=[C:4]([CH3:28])[CH:3]=1>[Pd].CO>[NH2:22][C:10]1[CH:9]=[CH:8][C:7]([O:6][C:5]2[CH:25]=[C:26]([CH3:27])[C:2]([OH:1])=[CH:3][C:4]=2[CH3:28])=[CH:12][C:11]=1[N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]

Participants

4

Reactant 1

HCID 18461383t-butyl N-[5-(4-hydroxy-2,5-dimethylphenoxy)-2-nitrophenyl]-N-methylcarbamate

Product 1

HCID 18461389t-Butyl N-[2-amino-5-(4-hydroxy-2,5-dimethylphenoxy)phenyl]-N-methylcarbamateYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a similar manner to that described in Reference Example 7, a reaction was carried out using t-butyl N-[5-(4-hydroxy-2,5-dimethylphenoxy)-2-nitrophenyl]-N-methylcarbamate (1.73 g), palladium on carbon (10%, 0.17 g) and methanol (50 ml) and the reaction mixture was purified to give the title compound (1.44 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-edc50d718fd64f559a577186742f0904
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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