Ethylenediamine → HCID 18448975, compound

HRID 1270069Notes

Reaction equation

HRID 1270069 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:19]([OH:21])=[O:20])=[CH:8][N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH2:23]([NH2:26])[CH2:24][NH2:25].C(Cl)Cl>CN1CCCC1=O.CO>[NH2:25][CH2:24][CH2:23][NH:26][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:19]([OH:21])=[O:20])=[CH:8][N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6344DichloromethaneHCID 184489817-Chloro-1,4-dihydro-4-oxo-1-(phenylmethyl)-3-quinolinecarboxylic acid

Product 1

HCID 18448975HCID 18448975, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 7-chloro-1-benzyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.0 g) in 1-methyl-2-pyrrolidinone (10 mL) was added ethylenediamine (0.95 g). The mixture was heated at 130° C. for 10 h. The reaction mixture was cooled and poured into DCM (20 mL). The precipitate obtained was dispersed in MeOH, filtered to give the title compound (560 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe precipitate obtained
  3. filtrationfiltered

Sources & evidence

ORD record
ord-741851bb55e64d6f9181910cb6925cd3
Source dataset
uspto-grants-2007_04
Patent number
US07202221B2

Reaction notes

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