Ethyl orthoformate → 7-Chloro-3-methyl-3H-imidazo[4,5-h]quinoline

HRID 1680952Notes

Reaction equation

HRID 1680952 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH3:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([Cl:12])=[CH:7]2.[CH:15](OCC)(OCC)OCC>>[CH3:14][N:13]1[C:3]2[CH:4]=[CH:5][C:6]3[CH:7]=[C:8]([Cl:12])[CH:9]=[N:10][C:11]=3[C:2]=2[N:1]=[CH:15]1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 14802295HCID 14802295, compound

Product 1

HCID 148022967-Chloro-3-methyl-3H-imidazo[4,5-h]quinoline

Conditions

Temperature
0 °C

Procedure

24.9 g (0.12 mol) of 8-amino-3-chloro-7-methylaminoquinoline and 107 g (0.72 mol) of triethyl orthoformate are heated at 100° C. for 30 min. The mixture is then cooled to 0° C., and the precipitate (32 g) is filtered off with suction. The mother liquor is concentrated under reduced pressure, and the residue is recrystallized from ethyl acetate/petroleum ether. The two solids obtained in this way are identical. Yield: 48.5 g (82%); melting point 188° to 189° C.

Workup

  1. filtrationthe precipitate (32 g) is filtered off with suction
  2. concentrationThe mother liquor is concentrated under reduced pressure
  3. customthe residue is recrystallized from ethyl acetate/petroleum ether
  4. customThe two solids obtained in this way

Sources & evidence

ORD record
ord-f26232d5d7054dee91395a2e9957d7b7
Source dataset
uspto-grants-1992_12
Patent number
US05167695

Reaction notes

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