Dimethylformamide → HCID 178488815, compound

HRID 2289909Notes

Reaction equation

HRID 2289909 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=O.CN(C)C=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>O>[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:14]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][C:7]=3[O:12][CH3:13])=[O:16])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178488816HCID 178488816, compound

Product 1

HCID 178488815HCID 178488815, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
37 °C

Procedure

To a mixture of 0.50 g of 4-hydroxy-8-methoxy-3-quinolinecarboxylic acid (J. Amer. Chem. Soc., 68, 1268 (1946)) and 10 mL of dimethylformamide is added 0.41 g of carbonyldiimidazole. The mixture is stirred 20 h at 37° C. and then it is cooled to ° C. The mixture is treated with 0.25 mL of distilled water and stirred for 5 min. To the resulting solution is added 0.31 mL of 4-chlorobenzylamine. After stirring for 18 hours the mixture is warmed to 40° C. and stirred an additional 24 h. The solution is then cooled to 25° C. and it is diluted with 10 mL of distilled water. After minutes the precipitate is collected by filtration and it is washed with two successive 5 mL portions of 10% aqueous acetic acid. It is dried for 18 h in a stream of air at 25° C. This procedure yields the title compound as 485 mg of a tan solid.

Workup

  1. temperatureit is cooled
  2. stirringstirred for 5 min
  3. stirringAfter stirring for 18 hours the mixture
  4. temperatureis warmed to 40° C.
  5. stirringstirred an additional 24 h
  6. temperatureThe solution is then cooled to 25° C.
  7. filtrationAfter minutes the precipitate is collected by filtration and it
  8. washis washed with two successive 5 mL portions of 10% aqueous acetic acid
  9. customIt is dried for 18 h in a stream of air at 25° C

Sources & evidence

ORD record
ord-5ada3db435e240c58b0f1f4ac0da26e1
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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