HCID 10086103, compound → HCID 10061020, compound

HRID 728118Notes

Reaction equation

HRID 728118 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16]C(=O)C)=[C:12]([N+:20]([O-:22])=[O:21])[CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1>C(O)C.Cl>[CH3:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([N+:20]([O-:22])=[O:21])[CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 10086103HCID 10086103, compound

Product 1

HCID 10061020HCID 10061020, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 3-methyl-2-[2-(4-acetamido-3-nitrophenyl)ethyl]pyridine (12.0 g) in ethanol (100 ml) and 17% hydrochloric acid (100 ml) was heated at 80° to 85° C. for 6 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in water. The resultant solution was adjusted to pH 8.0 with aqueous 20% potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from a mixture of ethyl acetate and diethyl ether to give 3-methyl-2-[2-(4-amino-3-nitrophenyl)ethyl]pyridine (9.3 g).

Workup

  1. temperaturewas heated at 80° to 85° C. for 6 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was recrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-bde028514e1043dea807725e2ff60b41
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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