Sodium Methoxide → HCID 13958461, compound

HRID 255544Notes

Reaction equation

HRID 255544 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH3:23][O-:24].[Na+]>CO.O>[CH3:23][O:24][C:2]1[C:11]2[N:12]=[CH:13][N:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 13958413HCID 13958413, compound

Product 1

HCID 13958461HCID 13958461, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 3.6 g (0.0116 mole) of 4-chloro-1-(4-methoxyphenyl)-1H-imidazo[4,5-c]quinoline (from Example 109), 25.1 g (0.116 mole) of 25% sodium methoxide in methanol and 50 ml of methanol was heated its reflux temperature for one hour. Evaporation provided a residue which was diluted with 75 ml of water. The precipitate was separated by filtration, washed with water and recrystallized from ethanol to provide 4-methoxy-1-(4-methoxyphenyl)-1H-imidazo[4,5-c]quinoline, m.p. 180°-182° C. Analysis: Calculated for C18H15N3O2 : %C, 70.8; %H, 5.0; %N, 13.8; Found: %C, 70.6; %H, 5.0; %N, 13.9.

Workup

  1. temperaturewas heated its
  2. temperaturereflux temperature for one hour
  3. customEvaporation
  4. customprovided a residue which
  5. customThe precipitate was separated by filtration
  6. washwashed with water
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d787fc03500b48d499593ecb3b56673b
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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