Hydrochloric Acid → HCID 10570206, compound

HRID 977172Notes

Reaction equation

HRID 977172 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]([CH3:26])[CH2:22][CH2:23][CH2:24][NH2:25].Cl>C(OCC)(=O)C>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][NH:25][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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 546974683-Phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one

Product 1

HCID 10570206HCID 10570206, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7-Chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (1 g) and 3-dimethylaminopropylamine (30 ml) were heated together in a similar manner to that described for Example 10 to give the crude product, which was suspended in a mixture of 1:1 ethyl acetate and 1N HCl and filtered. The aqueous phase was basified to pH14 with sodium hydroxide and then extracted into ethyl acetate. The organic layer was dried (MgSO4) and the solvent was removed to give the title compound (0.090 g); mp 177°-179° C. (diethyl ether). Found: C, 67.27; H, 6.22; N, 11.61. C20H22ClN3O requires C, 67.50; H, 6.23; N, 11.81%; δ (360 MHz, DMSO-d6) 1.38 (2H, m, NCH2CH2CH2N(CH3)2), 1.98 (2H, m, NCH2CH2CH2N(CH3)2), 2.04 (6H, s, N(CH3)2), 2.58 (2H, m, NCH2CH2CH2N(CH3)2), 6.58 (1H, m, NHCH2CH2CH2N), 7.19-7.94 (8H, m, aromatics), 11.15 (1H, br s, NHCO); m/z (CI-) 355 (M+).

Workup

  1. customto give the crude product, which
  2. filtrationfiltered
  3. extractionextracted into ethyl acetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-8400c6e64b324ef1b9600936b137a40f
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

Loading…