HCID 10012728, compound → 2-(1,2-Oxazol-5-yl)aniline

HRID 1816298Notes

Reaction equation

HRID 1816298 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][N:13]=[CH:12][CH:11]=1)([O-])=O>Cl>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][N:13]=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 10012728HCID 10012728, compound

Product 1

HCID 134898092-(1,2-Oxazol-5-yl)anilineYield 30.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
105 °C

Procedure

5-(2-nitrophenyl)isoxazole (850 mg, 4.5 mmol), prepared as in Example 101, was added portionwise to a suspension of stannous chloride dihydrate (3.3 g, 14.6 mmol) in concentrated hydrochloric acid (8.3 mL). The reaction was heated to 105° C. four 1 hour. The reaction was cooled to 10° C. and filtered, and the solid was added to water (10 mL). The solution was adjusted to pH 10 with 10N sodium hydroxide, and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give 5-(2-aminophenyl)isoxazole (220 mg), which was coupled with CMI under conditions described in the general procedure for CMI coupling to give the hydrochloric acid salt of N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-(5-isoxazolyl)aniline.

Workup

  1. temperatureThe reaction was cooled to 10° C.
  2. filtrationfiltered
  3. additionthe solid was added to water (10 mL)
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-519872ce0a6d49cb8310d9c893aa5573
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

Loading…