Acetic Acid → HCID 20152418, compound

HRID 4405Notes

Reaction equation

HRID 4405 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:25])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[N:12]=1.C(O)(=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:25])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)[N:12]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 137139694-{2-[2-(2-Chlorophenyl)-5-methyl-4-oxazolyl]ethoxy}nitrobenzene

Product 1

HCID 20152418HCID 20152418, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Reduced iron (10.6 g) was added portionwise mixture of 4-{2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy}nitrobenzene (22.9 g), acetic acid (150 ml) and water (50 ml) at 70° C. After stirring at 80° C. for 2 hours, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Water was added to the filtrate, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated to give 4-{2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy}aniline as a crude oily material (20.5 g, 97.6%). NMR δppm in CDCl3 : 2.35(3H, s), 2.93(2H, t, J=7 Hz), 3.77(2H, s), 4.15(2H, t, J=7 Hz), 6.56(2H, d, J=9 Hz), 6.75(2H, d, J= 9 Hz), 7.2 to 7.5(3H, m), 7.9 (1H, m).

Workup

  1. filtrationthe insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater was added to the filtrate
  4. extractionthe aqueous mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4df1147214394778b695246102bc2d3e
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Reaction notes

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