Nitric Acid → HCID 20463977, compound

HRID 325673Notes

Reaction equation

HRID 325673 reaction equation
[C:1]([NH:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH2:7]1)(=[O:4])[CH2:2][CH3:3].FC(F)(F)C(O)=O.[N+:25]([O-])([OH:27])=[O:26]>O.C(OCC)C>[C:1]([NH:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[C:12]=2[N+:25]([O-:27])=[O:26])[CH2:7]1)(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 20463976HCID 20463976, compound

Product 1

HCID 20463977HCID 20463977, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

12.2 g of 2-propanoylamino-6-methoxy-1,2,3,4-tetrahydronaphthalene are introduced into 100 ml of trifluoroacetic acid, and 3 ml of nitric acid (d=1.49) are added dropwise thereto. Stirring is continued for 8 hours and the mixture is then taken up in water and diethyl ether. To separate the nitro isomers, the mixture is subjected to chromatography under pressure, on a silica column, elution being carried out with an 8/2 methylene chloride/ethyl acetate mixture. 5 g of the isomer nitrated in the 7-position and 3.8 g of the isomer nitrated in the 5-position are finally collected.

Workup

  1. additionare added dropwise
  2. customTo separate the nitro isomers
  3. washthe mixture is subjected to chromatography under pressure, on a silica column, elution
  4. customare finally collected

Sources & evidence

ORD record
ord-90843f474a33404aa87ab595b665b412
Source dataset
uspto-grants-1984_04
Patent number
US04442126

Reaction notes

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