Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate → Methyl 4-[(2,6-diaminophenyl)amino]-3-hydroxybutanoate

HRID 1398802Notes

Reaction equation

HRID 1398802 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[NH:13][CH2:14][CH:15]([OH:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18])([O-])=O>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH:13][CH2:14][CH:15]([OH:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 1

HCID 86632868Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate

Product 1

HCID 68737495Methyl 4-[(2,6-diaminophenyl)amino]-3-hydroxybutanoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under hydrogen gas atmosphere, a mixture of methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate (Reference Example 79; 2.53 g, 8.45 mmol), 10% palladium on carbon (50% wet, 500 mg) and tetrahydrofuran (85 mL) was stirred at room temperature for 6 hr. The reaction mixture was filtered and concentrated in vacuo to give the title compound as a solid (2.00 g, 8.36 mmol, 99%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5170cf71512548fa8cd9d1aa4c5baea9
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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