Propargyl bromide → HCID 19965418, compound

HRID 977182Notes

Reaction equation

HRID 977182 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([OH:23])=[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12](=[O:16])[NH:13]2)=[CH:8][CH:7]=1>>[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([O:23][CH2:3][C:2]#[CH:1])=[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12](=[O:16])[NH:13]2)=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 7842Propargyl bromideHCID 546974683-Phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one

Product 1

HCID 19965418HCID 19965418, compound

Procedure

This was prepared as for Example 24 but using propargyl bromide (0.48 g, 0.0044 mol) and 7-chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (0.50 g, 0.0018 mol) and recrystallising the product from ethanol/water; yield=210 mg as a white crystalline solid, mp=183°-185° C. Found: C, 69.21; H, 3.68; N, 4.34. C18H12ClNO2 +0.1 H2O requires C, 69.39; H, 3.95; N, 4.50. δ (360 MHz, DMSO-d6), 3.50 (1H, t, J=2.3 Hz, CCH), 4.26 (2H, d, J=2.5 Hz, OCH2C), 7.28 (1H, dd, J=8.5 and 1.9 Hz, H6), 7.32-7.48 (6H, m, aromatics), 7.86 (1H, d, J=8.6 Hz, H5), 11.96 (1H, s, br, NH). MS (CI) m/z=310 [MH]+.

Workup

  1. customThis was prepared as for Example 24
  2. customrecrystallising the product from ethanol/water

Sources & evidence

ORD record
ord-c70a72e5c81a47f2a544b787d324cf0b
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

Loading…