Acetic Acid → HCID 18448968, compound

HRID 1270068Notes

Reaction equation

HRID 1270068 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14](Cl)=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([C:20]([OH:22])=[O:21])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH2:26])[CH2:24][NH2:25].O.C(O)(=O)C>CN1CCCC1=O>[NH2:25][CH2:24][CH2:23][NH:26][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]=[C:10]([C:20]([OH:22])=[O:21])[C:11]2=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3301EthylenediamineHCID 3793602HCID 3793602, compound

Product 1

HCID 18448968HCID 18448968, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-Benzyl-6-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (300 mg) in 1-methyl-2-pyrrolidinone (6 mL) was added ethylenediamine (170 mg) under argon atmosphere. The mixture was heated at 120° C. for 18 h and then at 145° C. for 4 h. The reaction mixture was cooled and poured into water (12 mL). The pH value was adjusted with acetic acid to 7.0–7.5. The reaction mixture was extracted with DCM (5×30 mnL). The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica SPE-column (eluent: from DCM 100% to DCM/MeOH/NH4OH 85/13/2) giving the title compound (80 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe reaction mixture was extracted with DCM (5×30 mnL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica SPE-column (eluent: from DCM 100% to DCM/MeOH/NH4OH 85/13/2)

Sources & evidence

ORD record
ord-11786446c9f24c4e9a6695f7d5b97340
Source dataset
uspto-grants-2007_04
Patent number
US07202221B2

Reaction notes

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