Nitric Acid → HCID 20463965, compound

HRID 325670Notes

Reaction equation

HRID 325670 reaction equation
[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].[N+:17]([O-])([OH:19])=[O:18]>O>[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:17]([O-:19])=[O:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10082161HCID 10082161, compound

Product 1

HCID 20463965HCID 20463965, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 g of 2-acetylamino-6-methoxy-1,2,3,4-tetrahydronaphthalene are introduced in small amounts into 600 ml of nitric acid (d=1.38), the temperature being kept between -5° and -10° C. The reaction has ended when total dissolution has taken place. The solution is then poured into 2 liters of water and ice and the solid is filtered off, washed and dried. This gives a mixture of the two mononitro isomers, the one being nitrated in the 5-position and the other in the 7-position, and of the dinitro compound. They are separated on a silica column with a 99/1 methyl ethyl ketone/methanol mixture. The compound nitrated in the 7-position melts at 175° C.

Workup

  1. custombeing kept between -5° and -10° C
  2. dissolutionwhen total dissolution
  3. filtrationthe solid is filtered off
  4. washwashed
  5. customdried
  6. customThis gives
  7. additiona mixture of the two mononitro isomers
  8. customThey are separated on a silica column with a 99/1 methyl ethyl ketone/methanol mixture

Sources & evidence

ORD record
ord-2f2a5ec5d8eb4e0896f5a90bf4115924
Source dataset
uspto-grants-1984_04
Patent number
US04442126

Reaction notes

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