Acetic Acid → HCID 18989579, compound

HRID 2395705Notes

Reaction equation

HRID 2395705 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][N:18]=1.C(O)(=O)C>[Fe].O>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[Cl:13])[O:6][C:2]=2[CH3:1])=[N:18][CH:19]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18989556HCID 18989556, compound

Product 1

HCID 18989579HCID 18989579, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-[2-[5-methyl-2-(2-chlorophenyl)-4-oxazolyl]ethoxy]-5-nitropyridine (1.69 g), iron dust (787 mg), acetic acid (25 ml) and water (8 ml) was stirred at 65°-70° C. for 3 hours. Insolubles were filtered off and the filtrate was evaporated under reduced pressure. To the residue was added water. The mixture was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate. The solvent was distilled off, and the residue was subjected to silica gel chromatography. From the fraction eluted with methanol-chloroform (1:25, v/v), 5-amino-2-[2-[5-methyl-2-(2-chlorophenyl)-4-oxazolyl]ethoxy]pyridine (1.50 g, 97%) was obtained.

Workup

  1. filtrationInsolubles were filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. additionTo the residue was added water
  4. extractionThe mixture was subjected to extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. washFrom the fraction eluted with methanol-chloroform (1:25

Sources & evidence

ORD record
ord-3a238178bb0643d1987b49ab3afd7f48
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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