Nitric Acid → HCID 20566313, compound

HRID 848166Notes

Reaction equation

HRID 848166 reaction equation
S(=O)(=O)(O)O.[C:6]1([CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:21]([O-])([OH:23])=[O:22].[OH-].[K+]>C(O)(=O)C>[N+:21]([C:9]1[CH:8]=[CH:7][C:6]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 14797Potassium HydroxideHCID 749374-(3-Phenylpropyl)pyridine

Product 1

HCID 20566313HCID 20566313, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

Into a solution consisting of 10.3 ml of pure acetic acid and 18.6 ml of 98% sulfuric acid, cooled to 5° C., are introduced slowly, drop by drop, 25 g of 4-(3-phenylpropyl) pyridine. When this addition has been completed, the solution obtained is cooled to -15° C. and a sulfonitric mixture consisting of 9 ml of nitric acid and 18.6 ml of 98% sulfuric acid is added drop by drop. During the whole of the addition the temperature of the reaction medium is maintained below +10° C. The addition is completed in one hour. The yellow solution obtained is poured into 600 g of a water+ice mixture. The pH is adjusted to 11 by the addition of an aqueous potassium hydroxide solution and the mixture is extracted twice with 200 ml of ether. The ethereal phases are collected and washed with water, dried over magnesium sulfate and concentrated. 29.7 g of 4-[3-(4-nitrophenyl)propyl]pyridine are obtained.

Workup

  1. additionare introduced slowly
  2. additionWhen this addition
  3. customthe solution obtained
  4. temperatureis cooled to -15° C.
  5. additionis added drop by drop
  6. additionDuring the whole of the addition the temperature of the reaction medium
  7. temperatureis maintained below +10° C
  8. additionThe addition
  9. customThe yellow solution obtained
  10. extractionthe mixture is extracted twice with 200 ml of ether
  11. customThe ethereal phases are collected
  12. washwashed with water
  13. dry with materialdried over magnesium sulfate
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-3dc93d6a97c74b058808ae595f75ee46
Source dataset
uspto-grants-1981_10
Patent number
US04294841

Reaction notes

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