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

HRID 1628468Notes

Reaction equation

HRID 1628468 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]>O1CCCC1.[Pd]>[NH2:16][C:15]1[C:6]([NH:5][CH2:4][CH2:3][CH2:2][OH:1])=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 68737547Methyl 2-[(3-hydroxypropyl)amino]-3-nitrobenzoate

Product 1

HCID 68736607Methyl 3-amino-2-[(3-hydroxypropyl)amino]benzoateYield 78.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[(3-hydroxypropyl)amino]-3-nitrobenzoate (86.6 g, 0.341 mol) in tetrahydrofuran (1000 mL) was added 10% palladium on carbon (50% wet; 8.70 g), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 23 hr. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound (59.8 g, 0.267 mol, 78%).

Workup

  1. customthe mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3f14bdac5a774d58a17dc5388221db4a
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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