Acetic Acid → HCID 20200495, compound

HRID 979518Notes

Reaction equation

HRID 979518 reaction equation
CS[C:3]1[NH:4][C:5]2[C:6]([N:19]=1)=[N:7][C:8]1[CH:9]=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:11]=[CH:12][C:13]=1[CH:14]=2.C(O)(=[O:22])C.Cl>O>[F:16][C:15]([F:18])([F:17])[C:10]1[CH:11]=[CH:12][C:13]2[CH:14]=[C:5]3[NH:4][C:3](=[O:22])[NH:19][C:6]3=[N:7][C:8]=2[CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 313Hydrochloric Acid2×HCID 20200507HCID 20200507, compound

Product 1

HCID 20200495HCID 20200495, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-(methylthio)-6-(trifluoromethyl)-1H-imidazo[4,5-b]quinoline (1.77 g, 6 mmol), acetic acid (25 mL) and 3N hydrochloric acid solution (25 mL) was heated on a steam bath for 4 hours. The solution was diluted with hot water (250 mL), cooled and filtered. The filtrate was concentrated to afford a second crop. Solids were combined with acetic acid (25 mL) and 3N hydrochloric acid solution (25 mL) and the mixture heated on a steam bath overnight. The mixture was diluted with hot water (250 mL), cooled, the solid collected and dried in vacuo to accord 1,3-dihydro-6-(trifluoromethyl)-2H-imidazo[4,5-b]quinolin-2-one (1.38 g, 83%), m.p. >250° C.

Workup

  1. temperaturewas heated on a steam bath for 4 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customto afford a second crop
  6. temperaturethe mixture heated on a steam bath overnight
  7. temperaturecooled
  8. customthe solid collected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-2c578d1c94b44302a362ae375bb9667f
Source dataset
uspto-grants-1987_05
Patent number
US04668686

Reaction notes

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