1-[(2,3-Dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]eth-2-yl acetate → 1-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]eth-2-yl Acetate

HRID 1245894Notes

Reaction equation

HRID 1245894 reaction equation
[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:13]([N+:14]([O-])=O)=[C:12]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:11]=[C:10]([CH3:24])[C:9]=1[CH3:25])(=[O:3])[CH3:2].[H][H]>[Pt].C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([CH3:25])=[C:10]([CH3:24])[N:11]=[C:12]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:13]=1[NH2:14])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 692100841-[(2,3-Dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]eth-2-yl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 691934021-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]eth-2-yl Acetate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

1-[(2,3-Dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]eth-2-yl acetate (11.5 g, 33.30 mmol) was combined with 5% platinum on carbon (5.0 g) in a Parr flask. Toluene was added to the flask (120 mL) and the resulting mixture was pressurized with hydrogen at 310 kPa at room temperature for 1.6 hours. The reaction was complete as determined by LC/MS and HPLC. The resulting reaction mixture was filtered through Celite™ filter agent, and the filter cake was rinsed with more toluene. The volatiles were removed under reduced pressure, and the resulting oil was carried on to the next step.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through Celite™
  3. filtrationfilter agent
  4. washthe filter cake was rinsed with more toluene
  5. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-a60e3dca94ac4c52a626db20946d7607
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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