Acetic Acid → HCID 15043300, compound

HRID 2393076Notes

Reaction equation

HRID 2393076 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([CH3:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.[Fe]>[CH3:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]([CH3:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 11430Potassium CarbonateHCID 15043299HCID 15043299, compound

Product 1

HCID 15043300HCID 15043300, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 702EthanolSolvent

Procedure

5,8-Dimethyl-6-aminoguinoline. To a solution of 5,8-dimethyl-6-nitroquinoline (1.41 g) in ethanol (17.4 mL) under argon is added iron (Fe) (1.21 g) and glacial acetic acid (2.56 g). The mixture is refluxed for two hours. More Fe (1.23 g) and glacial acetic acid (2.49 g) are added to the reaction, which is allowed to reflux for an additional hour. The reaction is poured into a beaker of ice and adjusted to pH 10 by careful addition of a saturated solution of potassium carbonate. The product is extracted with methylene chloride and the organic layer is dried over sodium sulfate, filtered, and rotary evaporated to give 5,8-dimethyl-6-aminoquinoline.

Workup

  1. temperatureThe mixture is refluxed for two hours
  2. temperatureto reflux for an additional hour
  3. additionThe reaction is poured into a beaker of ice
  4. extractionThe product is extracted with methylene chloride
  5. dry with materialthe organic layer is dried over sodium sulfate
  6. filtrationfiltered
  7. customrotary evaporated

Sources & evidence

ORD record
ord-4c553a97160741a886b43d53335be046
Source dataset
uspto-grants-1998_09
Patent number
US05804587

Reaction notes

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