HCID 69521999, compound → HCID 69523024, compound

HRID 856685Notes

Reaction equation

HRID 856685 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][S:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[CH3:21])[CH:5]=1)[CH3:2]>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][S:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[CH3:21])[CH:5]=1)[CH3:2]

Participants

3

Reactant 1

HCID 69521999HCID 69521999, compound

Product 1

HCID 69523024HCID 69523024, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-ethoxy-2-[[(2-methyl-4-nitrophenyl)sulfanyl]methyl]pyridine (2.5 g) was dissolved in acetic acid (25 ml), reduced iron (7.5 g) was added to the mixture, and the mixture was stirred for 420 hours at room temperature. The mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[[(4-ethoxy-2-pyridinyl)methyl]sulfanyl]-3-methylaniline (1.8 g).

Workup

  1. filtrationThe mixture was filtered with Celite
  2. washwashed with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7fe1d76407e541068269e47886a050f5
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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