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 1352546Notes

Reaction equation

HRID 1352546 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-fdcffd81894b42c88289e95d0bf59a66
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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