Nitric Acid → HCID 86626016, compound

HRID 870363Notes

Reaction equation

HRID 870363 reaction equation
[N:1]1([C:15](=[O:18])[CH2:16][CH3:17])[C@H:10]2[C@@H:5]([CH2:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[N+:19]([O-])([OH:21])=[O:20].O.S(=O)(=O)(O)O>[N+](C)([O-])=O>[N+:19]([C:13]1[CH:12]=[CH:11][C:8]2[CH2:9][C@@H:10]3[C@H:5]([CH2:4][CH2:3][CH2:2][N:1]3[C:15](=[O:18])[CH2:16][CH3:17])[CH2:6][C:7]=2[CH:14]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 86626015HCID 86626015, compound

Product 1

HCID 86626016HCID 86626016, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

2.5 g trans-1-(3,4,4a,5,10,10a-Hexahydro-2H-benzo[g]quinolin-1-yl)-propan-1-one (10.27 mmol) were dissolved in 25 ml nitromethane. At −5° C. to −10° C., a mixture of 0.71 ml of nitric acid (10.27 mmol), 1.5 ml of water, and 9.5 ml of sulphuric acid (170 mmol) were added within 30 minutes. Stirring continued for 1.5 h under cooling conditions before the mixture was poured onto crushed ice. The aqueous phase was extracted twice with ethyl acetate, the combined organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield 2.7 g of the nitrated product as a mixture of several nitro-isomers, which was used in the subsequent reaction without further separation.

Workup

  1. additionwere added within 30 minutes
  2. additionwas poured
  3. customonto crushed ice
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-983d86cc9b274100adbd3630d8075aaa
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

Loading…