t-Butyl N-methyl-N-[2-nitro-5-(4-phenoxyphenoxy)phenyl]carbamate → t-Butyl N-[2-amino-5-(4-phenoxyphenoxy)phenyl]-N-methylcarbamate

HRID 2303887Notes

Reaction equation

HRID 2303887 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:6][C:5]=1[N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])([O-])=O>[Pd].C1(C)C=CC=CC=1.CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)=[CH:6][C:5]=1[N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 18461359t-Butyl N-methyl-N-[2-nitro-5-(4-phenoxyphenoxy)phenyl]carbamate

Product 1

HCID 18461416t-Butyl N-[2-amino-5-(4-phenoxyphenoxy)phenyl]-N-methylcarbamateYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21867641Toluene methanolSolvent

Procedure

In a similar manner to that described in Reference Example 7, a reaction was carried out using t-butyl N-[2-nitro-5-(4-phenoxyphenoxy)phenyl]-N-methylcarbamate (8.6 g), palladium on carbon (10%, 0.6 g) and toluene/methanol=16/3 (190 ml) and the reaction mixture was purified to give the title compound (7.2 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-25a871967099458cbe50b5eb1f201e18
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

Loading…