2-Methyl-4-methoxyaniline → HCID 22466650, compound

HRID 1935161Notes

Reaction equation

HRID 1935161 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].[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([CH3:27])[CH:21]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[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][C:20]([O:19][CH3:18])=[CH:21][C:22]=1[CH3:27]

Participants

5

Reactant 3

HCID 76102-Methyl-4-methoxyanilineHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 22466650HCID 22466650, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A reaction mixture of 248.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 164.6 mg (1.2 mmol) of 4-methoxy-2-methyl-aniline and 115.6 mg (1 mmol) of pyridine hydrochloride in 10 mL of 2-ethoxyethanol was refluxed under N2 for 3 hr. After removal of the solvent, the residue was diluted with water and neutralized to pH 7-8 with diluted sodium carbonate solution. The precipitate was filtered and washed with water and ether. After drying in vacuo. this yielded 250.2 mg (71.7%) of the product as a off red solid, m.p.>131° C. (dec.), mass (electrospray, m/e): M+H 349.9.

Workup

  1. temperaturewas refluxed under N2 for 3 hr
  2. customAfter removal of the solvent
  3. additionthe residue was diluted with water and neutralized to pH 7-8 with diluted sodium carbonate solution
  4. filtrationThe precipitate was filtered
  5. washwashed with water and ether
  6. customAfter drying in vacuo

Sources & evidence

ORD record
ord-ea7cd1d636254ab7b853d948e985d731
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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