N,N-Dimethylethylenediamine → HCID 10545217, compound

HRID 977171Notes

Reaction equation

HRID 977171 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH2:24]>>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH:24][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:9][C:8](=[O:12])[C:7]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 546974683-Phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one

Product 1

HCID 10545217HCID 10545217, compound

Procedure

7-Chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (1 g) and N,N-dimethylethylenediamine (30 ml) were heated in a sealed tube at 180° C. for 10 days. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and saturated potassium carbonate solution. The organic layer was separated, dried (Na2SO4) and the solvent was removed under vacuum. The residue was dissolved in HCl, washed with diethyl ether (2×), then basified with sodium hydroxide, extracted into ethyl acetate, dried (MgSO4), and concentrated in vacuo, to give 0.248 g of the title compound; mp 230° C. (ethyl acetate); Found: C, 63.76; H, 5.64; N, 11.75.C19H2O ClN3O.0.9H2O requires C, 63.37; H, 6.14; N, 11.76%. δ (360 MHz, DMSO-d6) 1.94 (6H, s, (CH3)2N), 2.17 (2H, m, NCH2CH2N), 2.69 (2H, m, NCH2CH2N), 5.82 (1H, br s, NH), 7.17-7.95 (8H, m, aromatics), 11.23 (1H, br s, NH); m/z (CI+) 341 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and saturated potassium carbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed under vacuum
  6. dissolutionThe residue was dissolved in HCl
  7. washwashed with diethyl ether (2×)
  8. extractionextracted into ethyl acetate
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b8717afa3bc44f9956a2991acb48bfd
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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