Water → HCID 21406499, compound

HRID 1729904Notes

Reaction equation

HRID 1729904 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([CH3:19])[C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11](N)=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1.[OH2:21]>>[OH:21][C:12]1[CH:13]=[C:14]2[C:9]([C:8]3[CH:16]=[CH:17][C:5]([CH:4]([CH3:19])[C:3]([OH:2])=[O:20])=[CH:6][C:7]=3[CH2:15]2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 962WaterHCID 53764708HCID 53764708, compound

Product 1

HCID 21406499HCID 21406499, compound

Procedure

The ester is dissolved in water (300 ml) containing concentrated HCL (11 ml) with the aid of heat. The solution is cooled to 3°, stirred and treated dropwise with a solution of sodium nitrite (2.84 g) in water (15 ml) over a 30 minute period. The resulting diazonium solution is then added dropwise over a 1 hour period to boiling water (800 ml) containing concentrated sulfuric acid (13 ml), and then stirred for 30 minutes and cooled. The precipitate is collected by filtration and heated in 10% aqueous potassium hydroxide containing charcoal for 1 hour, cooled and acidified with 4N HCl. The solid is collected by filtration to give 8.0 g, mp 205°-207° of the titled product. The analytical sample is prepared by sublimation, mp 218-219°.

Workup

  1. additioncontaining
  2. concentrationconcentrated HCL (11 ml) with the aid
  3. temperatureof heat
  4. temperatureThe solution is cooled to 3°
  5. additiontreated dropwise with a solution of sodium nitrite (2.84 g) in water (15 ml) over a 30 minute period
  6. additionThe resulting diazonium solution is then added dropwise over a 1 hour period
  7. additioncontaining concentrated sulfuric acid (13 ml)
  8. stirringstirred for 30 minutes
  9. temperaturecooled
  10. filtrationThe precipitate is collected by filtration
  11. temperatureheated in 10% aqueous potassium hydroxide
  12. additioncontaining charcoal for 1 hour
  13. temperaturecooled
  14. filtrationThe solid is collected by filtration

Sources & evidence

ORD record
ord-318c4086aa95408dbbd69689ea220f39
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

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