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

HRID 1398822Notes

Reaction equation

HRID 1398822 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 as a brown oil (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-f8a6c8756dae4e10b091933a929cb646
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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