Ethanol → HCID 19018617, compound

HRID 1110032Notes

Reaction equation

HRID 1110032 reaction equation
[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+:14]([O-:16])=[O:15])=[CH:5][C:4]=3[C:3]=1[CH2:17][C:18]([OH:20])=[O:19].S(=O)(=O)(O)O.[CH2:26](O)[CH3:27]>>[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+:14]([O-:16])=[O:15])=[CH:5][C:4]=3[C:3]=1[CH2:17][C:18]([O:20][CH2:26][CH3:27])=[O:19]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 10333535HCID 10333535, compound

Product 1

HCID 19018617HCID 19018617, compound

Procedure

44.5 g of 5,6-dihydro-2-methyl-8-nitro-4H-pyrrolo[3,2,1-ij]quinoline-1-acetic acid (preparation see Example 20 A) were heated under reflux for 1 hour in 450 ml of ethanol after addition of 8.63 ml of sulfuric acid. To work up the reaction mixture the ethanol was removed by evaporation, the residue was taken up in a mixture of water and dichloromethane, and the organic phase was separated, washed with water until neutral, dried and evaporated. Some diethyl ether was added to the oily crude product which remained as a residue, and the resulting precipitate was filtered out. 32.4 g of ethyl 5,6-dihydro-2-methyl-8-nitro-4H-pyrrolo[3,2,1-ij]quinoline-1-acetate were obtained as a greenish-ochre-colored powder.

Workup

  1. temperaturewere heated
  2. customwas removed by evaporation
  3. additionthe residue was taken up in a mixture of water and dichloromethane
  4. customthe organic phase was separated
  5. washwashed with water until neutral,
  6. customdried
  7. customevaporated
  8. additionSome diethyl ether was added to the oily crude product which
  9. filtrationthe resulting precipitate was filtered out

Sources & evidence

ORD record
ord-796df5a738434889b44022f4b44c4a7d
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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