Ammonia → HCID 19593050, compound

HRID 613493Notes

Reaction equation

HRID 613493 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[O:14][CH2:15][CH3:16])=[CH:11][CH:10]=[CH:9][C:8]=2[NH:17][C:18](=[O:27])[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])(O)=[O:2].Cl.C([N:31]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.N>CN(C)C=O.O>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[O:14][CH2:15][CH3:16])=[CH:11][CH:10]=[CH:9][C:8]=2[NH:17][C:18](=[O:27])[C:19]1[C:20]([Cl:26])=[CH:21][CH:22]=[CH:23][C:24]=1[Cl:25])(=[O:2])[NH2:31]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19592608HCID 19592608, compound

Product 1

HCID 19593050HCID 19593050, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-carboxy-8-(2,6-dichlorobenzoylamino)-4-ethoxyquinoline (153 mg) in dimethylformamide were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (109 mg) and 1-hydroxybenzotriazole (76.5 mg), and the mixture was stirred for 2 hours at ambient temperature. To the mixture was added conc. ammonia solution (0.2 ml) with stirring, and the mixture was stirred for 6 hours at ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride solution, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethanol to give 3-carbamoyl-8-(2,6-dichlorobenzoylamino)-4-ethoxyquinoline (128.3 mg).

Workup

  1. stirringwith stirring
  2. stirringthe mixture was stirred for 6 hours at ambient temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated ammonium chloride solution, saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-0552311f8158438989fa57746e7fb53d
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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