Nitric Acid → 1-Nitropyrene

HRID 1287205Notes

Reaction equation

HRID 1287205 reaction equation
[CH:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[N+:17]([O-])([OH:19])=[O:18]>C(O)(=O)C.O>[N+:17]([C:8]1[C:7]2[C:16]3=[C:15]4[C:4](=[CH:5][CH:6]=2)[CH:3]=[CH:2][CH:1]=[C:14]4[CH:13]=[CH:12][C:11]3=[CH:10][CH:9]=1)([O-:19])=[O:18]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 31423Pyrene

Product 1

HCID 216941-Nitropyrene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution was prepared by dissolving 101 g of pyrene in 800 ml of glacial acetic acid. While heating this solution at 50° C. in water bath with stirring, a mixed solution of 42 ml of nitric acid (D=1.4) and 50 ml of glacial acetic acid was slowly added thereto dropwise. At the end of 30 minutes, the reacted mixture was filtered with suction. The precipitate was washed with a small quantity of glacial acetic acid and then thoroughly washed with water to obtain 115 g of yellow crystals (melting point: 150° C.). By recrystallizing these crystals in glacial acetic acid, crystals having a melting point in the range of 153°~154° C. were obtained. The result of elemental analysis of this product was as shown in the following table:

Workup

  1. customA solution was prepared
  2. filtrationAt the end of 30 minutes, the reacted mixture was filtered with suction
  3. washThe precipitate was washed with a small quantity of glacial acetic acid
  4. washthoroughly washed with water

Sources & evidence

ORD record
ord-3dc778c6de244e158cd4526e133ee694
Source dataset
uspto-grants-1976_10
Patent number
US03984378

Reaction notes

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