t-Butyl N-methyl-N-[2-nitro-5-(3-phenylphenoxy)phenyl]carbamate → t-Butyl N-[2-amino-5-(3-phenylphenoxy)phenyl]-N-methylcarbamate

HRID 2303889Notes

Reaction equation

HRID 2303889 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=2)=[CH:6][C:5]=1[N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])([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:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=2)=[CH:6][C:5]=1[N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]

Participants

4

Reactant 1

HCID 18461261t-Butyl N-methyl-N-[2-nitro-5-(3-phenylphenoxy)phenyl]carbamate

Product 1

HCID 18461320t-Butyl N-[2-amino-5-(3-phenylphenoxy)phenyl]-N-methylcarbamateYield 75%

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-(3-phenylphenoxy)phenyl]-N-methylcarbamate (8.7 g), palladium on carbon (10%, 0.69 g) and toluene/methanol=7/3 (100 ml) and the reaction mixture was purified to give the title compound (6.06 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-0478a11173284368b4d6f43712ad7e7f
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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