HCID 18461411, compound → t-Butyl N-[2-amino-5-(4-methoxymethoxy-2,3,5-trimethylphenoxy)phenyl]N-methylcarbamate

HRID 2303841Notes

Reaction equation

HRID 2303841 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:29]([CH3:30])=[CH:28][C:8]([O:9][C:10]2[CH:11]=[CH:12][C:13]([N+:25]([O-])=O)=[C:14]([N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)=[C:7]([CH3:31])[C:6]=1[CH3:32]>[Pd].CO>[NH2:25][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:8]2[CH:28]=[C:29]([CH3:30])[C:5]([O:4][CH2:3][O:2][CH3:1])=[C:6]([CH3:32])[C:7]=2[CH3:31])=[CH:15][C:14]=1[N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 18461411HCID 18461411, compound

Product 1

HCID 18461355t-Butyl N-[2-amino-5-(4-methoxymethoxy-2,3,5-trimethylphenoxy)phenyl]N-methylcarbamateYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 57.0 g of t-butyl N-[5-(4-methoxymethoxy-2,3,5-trimethylphenoxy)-2-nitrophenyl]-N-methylcarbamate, 3 g of 10% palladium on carbon and 500 ml of methanol was vigorously stirred at room temperature for 8 hours under a hydrogen atmosphere. The palladium on carbon in the reaction mixture was filtered off and the filtrate was concentrated by evaporation. The residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=3/1), whereby 52.5 g of the title compound were obtained.

Workup

  1. filtrationThe palladium on carbon in the reaction mixture was filtered off
  2. concentrationthe filtrate was concentrated by evaporation
  3. customThe residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-1a875443768c4e1e83146b285547d559
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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