Formic Acid → 1H-Imidazo[4,5-c]quinoline, 1-methyl-

HRID 2165548Notes

Reaction equation

HRID 2165548 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:14](O)=O>>[CH3:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:14]1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 13958346HCID 13958346, compound

Product 1

HCID 139583741H-Imidazo[4,5-c]quinoline, 1-methyl-Yield 77%

Procedure

A solution of 2.92 g of 3-amino-4-methylaminoquinoline (V-2) in 20 ml of formic acid was refluxed for 1.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between chloroform and saturated aqueous sodium hydrogen-carbonate. The organic layer was washed with brine and dried. The chloroform was removed and the residue was crystallized from n-hexane to give 2.39 g (yield: 77%) of the titled compound (II-2). This was recrystallized from ethyl acetate to give colorless crystals melting at 146°~148° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between chloroform and saturated aqueous sodium hydrogen-carbonate
  3. washThe organic layer was washed with brine
  4. customdried
  5. customThe chloroform was removed
  6. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-17d6d76daa534459b5fbbf69d3be4f9a
Source dataset
uspto-grants-1990_07
Patent number
US04940714

Reaction notes

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