1,1'-Carbonyldiimidazole → HCID 178523947, compound

HRID 2289906Notes

Reaction equation

HRID 2289906 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:14]([OH:16])=O)=[C:5]2[OH:17].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][NH2:39])=[CH:34][CH:33]=1>CN(C)C=O.O.C(N(CC)CC)C>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][NH:39][C:14]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[OH:17])=[CH:3][C:2]([F:1])=[C:11]([F:12])[C:10]=3[F:13])=[O:16])=[CH:34][CH:33]=1

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 178524735HCID 178524735, compound

Product 1

HCID 178523947HCID 178523947, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 1.0 g of 6,7,8-trifluoro-4-hydroxy-3-quinolinecarboxylic acid (J. Amer. Chem. Soc., 68, 1264 (1946)). (The sample used in this procedure was shown by Karl Fisher titration to be a hydrate containing 0.4 equivalents of water.) in 15 mL of a 99:1 (v/v) mixture of dimethylformamide and triethylamine is added 1.01 g of carbonyldiimidazole. The mixture is stirred for 3 days and then it is transferred to a volumetric flask and diluted with dimethylformamide to a total volume of 25 mL. To 1.22 mL of this solution is added 39 mg of 4-chlorophenyl-hydrazine hydrochloride. The mixture is stirred 18 h at 25° C. and then 15 mL of distilled water is added. The precipitate is collected by filtration and dried in a stream of air. This procedure gives the title compound as 45 mg of a solid.

Workup

  1. customit is transferred to a volumetric flask
  2. stirringThe mixture is stirred 18 h at 25° C.
  3. filtrationThe precipitate is collected by filtration
  4. customdried in a stream of air

Sources & evidence

ORD record
ord-da6b652ed691480cab7b6a581c9cdcbc
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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