Ethylenediamine → HCID 12034150, compound

HRID 1270071Notes

Reaction equation

HRID 1270071 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH2:19]([NH2:22])[CH2:20][NH2:21].C(Cl)Cl>CN1CCCC1=O.CO>[NH2:21][CH2:20][CH2:19][NH:22][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6344DichloromethaneHCID 133851637-Chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 12034150HCID 12034150, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 7-chloro-1-cyclopropyl-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (2.0 g) in 1-methyl-2-pyrrolidinone (20 mL) was added ethylenediamine (2.3 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 (910 mg).

Workup

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

Sources & evidence

ORD record
ord-1268e7fc720241f0826694e059da8ec1
Source dataset
uspto-grants-2007_04
Patent number
US07202221B2

Reaction notes

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