tert-Butyl (2-((5-methoxy-2-nitrophenyl)amino)ethyl)carbamate → Carbamic acid, N-[2-[(2-amino-5-methoxyphenyl)amino]ethyl]-, 1,1-dimethylethyl ester

HRID 1916892Notes

Reaction equation

HRID 1916892 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[N+:19]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2].O1CCOCC1>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[NH2:19])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59345555tert-Butyl (2-((5-methoxy-2-nitrophenyl)amino)ethyl)carbamate

Product 1

HCID 59345530Carbamic acid, N-[2-[(2-amino-5-methoxyphenyl)amino]ethyl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 2 L round bottom flask equipped with a stir bar was charged with a suspension of 20% Pd(OH)2 (5 g) and 1,4-dioxane (800 mL). [2-(5-Methoxy-2-nitrophenylamino)-ethyl]-carbamic acid tert-butyl ester (100 g, 0.32 mol) was added to the suspension. The reaction mixture was hydrogenated (balloon) for 48 h (until the starting material had been consumed) followed by the addition of K2CO3 (100 g) was added to the mixture and stirred for an additional 12 h to remove traces of water. The suspension was filtered to remove the Pd(OH)2 and K2CO3. The filtrate was used in the next step without further purification (yield not determined).

Workup

  1. customA 2 L round bottom flask equipped with a stir bar
  2. customfor 48 h
  3. customhad been consumed)
  4. additionfollowed by the addition of K2CO3 (100 g)
  5. additionwas added to the mixture
  6. customto remove traces of water
  7. filtrationThe suspension was filtered
  8. customto remove the Pd(OH)2 and K2CO3
  9. customThe filtrate was used in the next step without further purification (
  10. customyield not

Sources & evidence

ORD record
ord-8ad2f2fe6d3d4c069776cc879a7375af
Source dataset
uspto-grants-2013_12
Patent number
US08618155B2

Reaction notes

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