Water → HCID 14835390, compound

HRID 1199016Notes

Reaction equation

HRID 1199016 reaction equation
[N:1]1[O:2][C:3]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#N)=[CH:12][CH:11]=2)=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[OH2:19].[OH-:20].[Na+]>C(O)C>[N:1]1[O:2][C:3]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:20])=[O:19])=[CH:12][CH:11]=2)=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14835341HCID 14835341, compound

Product 1

HCID 14835390HCID 14835390, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.6 g (0.015 mole) of 4-(2,1-benzisoxazol-3-yl)benzeneacetonitrile in 75 ml of ethanol and 10 ml of 20% sodium hydroxide was heated at reflux under a nitrogen atmosphere overnight. The dark solution was cooled and poured into 600 ml of water. The solution was filtered and the filtrate was treated with charcoal. The mixture was filtered through Celite and the filtrate pH was adjusted to 7. The mixture was again filtered and the filtrate was made acidic with concentrated hydrochloric acid. The solid which precipitated was collected by filtration, washed with water, dried, and recrystallized from 2-propanol to yield 2.1 g (54%) of tan powder, m.p. 179°-181° C. with decomposition.

Workup

  1. temperatureat reflux under a nitrogen atmosphere overnight
  2. temperatureThe dark solution was cooled
  3. filtrationThe solution was filtered
  4. additionthe filtrate was treated with charcoal
  5. filtrationThe mixture was filtered through Celite
  6. filtrationThe mixture was again filtered
  7. customThe solid which precipitated
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customdried
  11. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-b4c8a17d93824c46a617ac0ee3fe2d5a
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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