3-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl ester → 3-(2-Amino-5-methyl-phenylamino)-hexanoic acid ethyl ester

HRID 1747308Notes

Reaction equation

HRID 1747308 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-])=O)[CH2:7][CH2:8][CH3:9])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[NH2:18])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 594976263-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl ester

Product 1

HCID 594975033-(2-Amino-5-methyl-phenylamino)-hexanoic acid ethyl esterYield 110.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 3-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl ester (1.4 g, 4.8 mmol) in MeOH (10 mL) was added a slurry of Pd/C (wet) (0.25 g) in MeOH. The reaction mixture was saturated with H2 balloon and stirred at room temperature for 2 h. When the reaction was complete, the reaction mixture was filtered through a pad of celite. The filtrate was concentrated to afford 1.4 g of the desired product as dark purplish oil. This product was used for the next reaction without further purification.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3faab4ed20c34003990e36cd07bb2b55
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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