3-Methoxyaniline → HCID 22466687, compound

HRID 548428Notes

Reaction equation

HRID 548428 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-quinoline-3-carbonitrile, 200 ml ethanol, and 3.0 ml (26.0 mmol) m-anisidine was heated to reflux under N2. Removed heat at 4½ 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 4½ 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-909a1026b43f407fa2983f6bfc543545
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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