Hydrochloric Acid → HCID 21406499, compound

HRID 972266Notes

Reaction equation

HRID 972266 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.Cl.N([O-])=[O:23].[Na+].S(=O)(=O)(O)O>O>[OH:23][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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 53764708HCID 53764708, compound

Product 1

HCID 21406499HCID 21406499, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

The ester is dissolved in water (300 ml) containing concentrated HCl (11ml) 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 tilted product. The analytical sample is prepared by sublimation, mp 218°-219°.

Workup

  1. temperatureof heat
  2. temperatureThe solution is cooled to 3°
  3. stirringstirred for 30 minutes
  4. temperaturecooled
  5. filtrationThe precipitate is collected by filtration
  6. temperatureheated in 10% aqueous potassium hydroxide
  7. additioncontaining charcoal for 1 hour
  8. temperaturecooled
  9. filtrationThe solid is collected by filtration

Sources & evidence

ORD record
ord-015706300392463aadf594b9fff26ee6
Source dataset
uspto-grants-1977_10
Patent number
US04052436

Reaction notes

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