Methanol → HCID 5328850, compound

HRID 1934963Notes

Reaction equation

HRID 1934963 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[N+:18]([C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24])([O-:20])=[O:19].CO.C([O-])(O)=O.[Na+]>COCCO>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]#[N:17])=[C:2]2[NH:24][C:23]1[CH:25]=[CH:26][CH:27]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 74233-NitroanilineHCID 516892Sodium BicarbonateHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 5328850HCID 5328850, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 0.500 g (2.00 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile and 0.332 g (2.41 mmol) of 3-nitroaniline in 6 mL of methyl cellosolve was refluxed under N2 for 8 hr. Methanol was added, followed by satd NaHCO3 (pH 8) and volatile material was removed. The residue was slurried with water, collected by filtration and dried. Recrystallization from ethanol gave 0.480 g of 6,7-dimethoxy-4-(3-nitrophenylamino)quinoline-3-carbonitrile as yellow crystals: mass spectrum (electrospray, m/e): M+H 351.0.

Workup

  1. customwas removed
  2. filtrationcollected by filtration
  3. customdried
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-ae5d37cfefd743bf81436a2ddf8fdfdd
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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