Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate → Methyl 3-amino-2-[(2-hydroxyethyl)amino]benzoate

HRID 1628563Notes

Reaction equation

HRID 1628563 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]>[Pd].O1CCCC1>[NH2:15][C:14]1[C:5]([NH:4][CH2:3][CH2:2][OH:1])=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 11253443Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate

Product 1

HCID 68739391Methyl 3-amino-2-[(2-hydroxyethyl)amino]benzoateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate (10.0 g, 41.6 mmol) and 10% palladium on carbon (0.10 g) in tetrahydrofuran (200 mL) was stirred under hydrogen atmosphere at room temperature for 24 hr. Catalyst was removed by filtration and the filtrate was concentrated in vacuo to give the title compound (36 mg, 0.090 mmol, 90%) as a pale yellow oil. This product was used next steps without purification.

Workup

  1. customCatalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0495816f75c24b8a932f9c7949daa732
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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