3-Methoxyaniline → HCID 22466687, compound

HRID 612079Notes

Reaction equation

HRID 612079 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1>C(O)C>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:25][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 22466687HCID 22466687, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-3-quinolinecarbonitrile, 200 ml ethanol, and 3.0 ml (26.0 mmol) m-anisidine was heated to reflux under N2. Removed heat at 4.5 hours and made basic with saturated sodium bicarbonate. Stripped solvents and azeotroped with ethanol. Slurried with hexane and collected crystals. Washed with water, dried in vacuo. Dissolved 5.94 g of crude product in 320 ml boiling ethyl acetate, stirred with Darco, filtered, stripped solvent, and dried in vacuo, giving about 5 g of yellow-orange solid: mass spectrum (electrospray m/e): M+H=291.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 4.5 hours
  5. customazeotroped with ethanol
  6. customSlurried with hexane and collected crystals
  7. washWashed with water
  8. customdried in vacuo
  9. dissolutionDissolved 5.94 g of crude product in 320 ml
  10. filtrationfiltered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-308ade840b3c470aa4b0f5f71d9f4ffb
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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