N-t-butoxycarbonyl-N-methyl-5-methoxy-2-nitroaniline → tert-butyl N-(2-amino-5-methoxyphenyl)-N-methylcarbamate

HRID 1061122Notes

Reaction equation

HRID 1061122 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[N+:17]([O-])=O)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H][H]>C1(C)C=CC=CC=1.[Pd]>[C:1]([O:5][C:6](=[O:20])[N:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[NH2:17])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 15544600N-t-butoxycarbonyl-N-methyl-5-methoxy-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 10198914tert-butyl N-(2-amino-5-methoxyphenyl)-N-methylcarbamateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of N-(5-methoxy-2-nitrophenyl)-N-methylcarbamic acid t-butyl ester (5.8 g) in toluene (55 ml) was added 7.5% palladium on carbon (1.2 g, which contain 50% water) and the air of the reaction vessel was replaced with nitrogen and the mixture was stirred under a hydrogen atmosphere at 40° C. for 3 hours. After the reaction the mixture was cooled to room temperature and the hydrogen in the reaction vessel was replaced with nitrogen. The palladium on carbon was removed by filtration and the filtrate was evaporated in vacuo to 22 ml. To this solution was slowly added methylcyclohexane (44 ml) and the precipitated crystals were filtered to give the title compound (4.4 g, yield 85%).

Workup

  1. customAfter the reaction the mixture
  2. temperaturewas cooled to room temperature
  3. customThe palladium on carbon was removed by filtration
  4. customthe filtrate was evaporated in vacuo to 22 ml
  5. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-1f4b53846efa4f4396707b32c0ab95e7
Source dataset
uspto-grants-2003_02
Patent number
US06525220B2

Reaction notes

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