HCID 86738432, compound → 2-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)-1H-indole

HRID 485315Notes

Reaction equation

HRID 485315 reaction equation
C1(N[N:8]=[C:9]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:13][O:14][C:15]=2[CH3:16])[CH3:10])C=CC=CC=1>O>[CH3:16][C:15]1[O:14][N:13]=[C:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11]=1[C:9]1[NH:8][C:17]2[C:22]([CH:10]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

3

Reactant 1

HCID 86738432HCID 86738432, compound

Product 1

HCID 128548642-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1350 grams of polyphosphoric acid at 100° to 110° C., there is added portionwise 89.3 g (0.307 mole) of 1-(5-methyl-3-phenyl-4-isoxazolyl)-1-ethanone phenyl hydrazone, while maintaining the temperature between 105° and 115° C. After addition is complete the mixture is stirred at 100° to 110° C. for 3 hours. The mixture is then poured onto ice and water and the resulting solid is filtered and washed with water. The solid is then dissolved in ether, washed with water, dried and evaporated partially and cooled in ice. The resulting solid is filtered and washed with cold ether to give 2-(5-methyl-3-phenyl-4-isoxazolyl)-indole; m.p. 145° to 146° C.

Workup

  1. temperaturewhile maintaining the temperature between 105° and 115° C
  2. additionAfter addition
  3. filtrationthe resulting solid is filtered
  4. washwashed with water
  5. dissolutionThe solid is then dissolved in ether
  6. washwashed with water
  7. customdried
  8. customevaporated partially
  9. temperaturecooled in ice
  10. filtrationThe resulting solid is filtered
  11. washwashed with cold ether

Sources & evidence

ORD record
ord-970c7d19cec94f22acf1cd40528093f4
Source dataset
uspto-grants-1985_08
Patent number
US04536499

Reaction notes

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