Ethylenediamine → HCID 18448978, compound

HRID 1270070Notes

Reaction equation

HRID 1270070 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][CH:3]=1.[CH2:18]([NH2:21])[CH2:19][NH2:20].C(Cl)Cl>CN1CCCC1=O.CO>[NH2:20][CH2:19][CH2:18][NH:21][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6344DichloromethaneHCID 156185627-Chloro-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 18448978HCID 18448978, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 7-chloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (1,7 g) in 1-methyl-2-pyrrolidinone (20 mL) was added ethylenediamine (2.1 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 (830 mg).

Workup

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

Sources & evidence

ORD record
ord-fd73f1d89c2d416f8a69704d9a495b97
Source dataset
uspto-grants-2007_04
Patent number
US07202221B2

Reaction notes

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