Acetic Acid → 4-(1,2-Oxazol-3-yl)aniline

HRID 1371827Notes

Reaction equation

HRID 1371827 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[CH:13][O:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C.Cl[Sn]Cl.[OH-].[Na+]>Cl>[O:12]1[CH:13]=[CH:14][C:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[N:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 6054383-(4-Nitrophenyl)isoxazole2×

Product 1

HCID 231185764-(1,2-Oxazol-3-yl)anilineYield 59.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-(4-Nitrophenyl)isoxazole (Intermediate 4, 8 g, 42 mmol) was added to acetic acid (126 ml) and then SnCl2 (39 g, 205 mmol) in HCl (42 ml) was added. The reaction was allowed to stir for 4 hours and then 1M NaOH was added to bring the solution to pH˜11. The water layer was extracted with EtOAc and then the organic layers were collected, dried over Na2SO4, and dried under vacuum to yield the product (4 g).

Workup

  1. extractionThe water layer was extracted with EtOAc
  2. customthe organic layers were collected
  3. dry with materialdried over Na2SO4
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a3bbdc4ff9384a248fa7b2f511fc8392
Source dataset
uspto-grants-2007_01
Patent number
US07157482B2

Reaction notes

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