HCID 13489807, compound → 2-(1,2-Oxazol-4-yl)aniline

HRID 1980781Notes

Reaction equation

HRID 1980781 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[N:12][O:13][CH:14]=1)([O-])=O>Cl>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[N:12][O:13][CH:14]=1

Participants

3

Reactant 1

HCID 13489807HCID 13489807, compound

Product 1

HCID 134898102-(1,2-Oxazol-4-yl)anilineYield 71.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a suspension of 108 g of stannous chloride dihydrate in 270 ml of concentrated hydrochloric acid was added portionwise 30 g of 4-(2-nitrophenyl)isoxazole prepared in Example 10 at less than 30° C. The suspension was stirred at about 20°-35° C. for 10 hours, then cooled to 10° C. and filtered. The solid was added to ice-water (400 ml), 50% NaOH was added to make the suspension basic to a pH of about 10, and the resultant suspension filtered. The solid was washed 3×100 ml of water and suction dried to give 18 g of the title compound; m.p. 48°-51° C.

Workup

  1. filtrationfiltered
  2. additionThe solid was added to ice-water (400 ml), 50% NaOH
  3. additionwas added
  4. filtrationthe resultant suspension filtered
  5. washThe solid was washed 3×100 ml of water and suction
  6. customdried

Sources & evidence

ORD record
ord-5b45295883da4644a6140bb54fe17464
Source dataset
uspto-grants-1985_04
Patent number
US04511392

Reaction notes

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