Methyl 3-((2-hydroxy-2-methylpropyl)amino)-4-nitrobenzoate → Methyl 4-amino-3-[(2-hydroxy-2-methylpropyl)amino]benzoate

HRID 592327Notes

Reaction equation

HRID 592327 reaction equation
[OH:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[C:8]([O:10][CH3:11])=[O:9]>[Pd].CCOC(C)=O>[NH2:15][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[NH:4][CH2:3][C:2]([OH:1])([CH3:18])[CH3:19]

Participants

4

Reactant 1

HCID 66690227Methyl 3-((2-hydroxy-2-methylpropyl)amino)-4-nitrobenzoate

Product 1

HCID 66693495Methyl 4-amino-3-[(2-hydroxy-2-methylpropyl)amino]benzoateYield 108.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 3-[(2-hydroxy-2-methylpropyl)amino]-4-nitrobenzoate (2.69 g, 10.03 mmol) and 10% palladium on carbon (2.13 g, 2.005 mmol, 10%) was added EtOAc (20.0 mL). Reaction was vacuumed and then filled with nitrogen (3×), ending with vacuuming and was then put under a hydrogen balloon. Reaction stirred at ambient temperature for 3 h. Mixture filtered through celite, washing with MeOH. Filtrate concentrated and used without further purification, giving the title compound (2.59 g): LC-MS [M+1]=239.3.

Workup

  1. customReaction
  2. additionfilled with nitrogen (3×)
  3. customReaction
  4. filtrationMixture filtered through celite
  5. washwashing with MeOH
  6. concentrationFiltrate concentrated
  7. customused without further purification

Sources & evidence

ORD record
ord-7c17f2eb882b4bfaa0d88f252690c9df
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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