Nitric Acid → HCID 10333535, compound

HRID 1110028Notes

Reaction equation

HRID 1110028 reaction equation
[CH3:1][C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=1[CH2:14][C:15]([OH:17])=[O:16].S(=O)(=O)(O)O.[N+:23]([O-])([OH:25])=[O:24]>ClCCl>[CH3:1][C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]([N+:23]([O-:25])=[O:24])=[CH:5][C:4]=3[C:3]=1[CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 10105217HCID 10105217, compound

Product 1

HCID 10333535HCID 10333535, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

20 g of 5,6-dihydro-2-methyl-4H-pyrrolo[3,2,1-ij]-quinoline-1-acetic acid (prepared by hydrolysis of its ethyl ester obtained by Example 1C)) were cautiously added to 50 ml of sulfuric acid cooled to 0° C. The nitrating acid (=mixture of 5.56 ml of concentrated sulfuric acid and 4.04 ml of concentrated nitric acid) was then added cautiously. The reaction mixture was allowed to react at a temperature of 0° C. for 1 hour and at room temperature for 2 hours. To work up the reaction mixture, it was added to 200 g of ice, and a precipitate formed. The reaction mixture was extracted with dichloromethane, and a part of the precipitate which formed dissolved in the dichloromethane phase. The dichloromethane phase was separated, and the residual precipitate which remained in the aqueous phase was filtered out, washed with water and dried. 7.54 g of 5,6-dihydro-2-methyl-8-nitro-4H-pyrrolo-[3,2,1-ij]quinoline-1-acetic acid were obtained as a greenish-yellow powder. The dichloromethane phase was washed with water, dried and concentrated. The residue which remained, which further contained acid in addition to oily impurities, was treated with about 25 ml of ethanol to remove the oily impurities and filtered. A further 3.23 g of the acid were thus obtained, so that the total yield was 10.8 g.

Workup

  1. additionwas then added cautiously
  2. customto react at a temperature of 0° C. for 1 hour and at room temperature for 2 hours
  3. customa precipitate formed
  4. extractionThe reaction mixture was extracted with dichloromethane
  5. customa part of the precipitate which formed
  6. customThe dichloromethane phase was separated
  7. filtrationwas filtered out
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-6164ee9ca1a540c9acfe1b168e554bfe
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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