Benzoyl chloride → HCID 86627508, compound

HRID 1969983Notes

Reaction equation

HRID 1969983 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:17][C:18]1[CH:27]=[CH:26][C:25]2[NH:24][C:23](=[O:28])[C:22]3[NH:29][CH:30]=[CH:31][C:21]=3[C:20]=2[CH:19]=1.[CH2:32]([C:34]([O-:36])=[O:35])[CH3:33]>CN(C)C=O>[C:8]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[NH:24][C:23](=[O:28])[C:22]3[NH:29][CH:30]=[CH:31][C:21]=3[C:20]=2[CH:19]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:32]([C:34]([O-:36])=[O:35])[CH3:33]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86627489HCID 86627489, compound

Product 1

HCID 86627508HCID 86627508, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

52 μL (0.37 mmol) of triethylamine and then 24 μL (0.20 mmol) of benzoyl chloride are added to 50 mg (0.18 mmol) of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 64) suspended in anhydrous dimethylformamide (1 mL). The solution is stirred for 2.5 h at 40° C. The solvent is evaporated and the residue obtained is purified by recrystallization from methanol to give 36 mg (52%) of 8-benzoylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. customThe solvent is evaporated
  2. customthe residue obtained
  3. customis purified by recrystallization from methanol

Sources & evidence

ORD record
ord-df811f3c275e41838bc138b1e411ecef
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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