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

HRID 1398920Notes

Reaction equation

HRID 1398920 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-737826156d394834a6b23843777963b0
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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