Benzylamine → HCID 11792906, compound

HRID 977173Notes

Reaction equation

HRID 977173 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.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([NH:27][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)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 546974683-Phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one

Product 1

HCID 11792906HCID 11792906, compound

Procedure

7-Chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (0.5 g) and benzylamine (20 ml) was heated under reflux for 24 h. The reaction was concentrated under high vacuum and the residue was triturated with diethyl ether and filtered. The filtrate was evaporated and purified by chromatography (25% ethyl acetate-dichloromethane eluent) to give the title compound as a white solid (0.045 g); mp 179° C. (diethyl ether). Found: C, 72.63; H, 4.45; N, 7.65. C22H17ClN2O.0.1H2O requires C, 72.87; H, 4.78; o N, 7.72%; δ (360 MHz, DMSO-d6) 3.81 (2H, d, J=4.8 Hz, PhCH2NH), 8.67 (1H, t, J=4.8 Hz, PhCH2NH), 6.85 (2H, d, J=6.5 Hz, ortho aromatics), 7.10-7.33 (11H, m, aromatics), 8.16 (1H, d, J=8.8 Hz, 5-H), 11.23 (1H, br s, NH); m/z (EI) 360 (M+).

Workup

  1. temperatureunder reflux for 24 h
  2. concentrationThe reaction was concentrated under high vacuum
  3. customthe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. custompurified by chromatography (25% ethyl acetate-dichloromethane eluent)

Sources & evidence

ORD record
ord-e1e6c63da0394e2c82952dba2323202b
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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