Water → HCID 10852545, compound

HRID 977184Notes

Reaction equation

HRID 977184 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:19])=[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.C(=O)([O-])O.[Na+].[CH2:25](Br)[CH:26]=[CH2:27].O>CN(C)C=O>[CH2:27]([O:19][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)[CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 546974683-Phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one

Product 1

HCID 10852545HCID 10852545, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (5.00 g) in dimethyl formamide (150 ml) under nitrogen at room temperature, was added sodium hydrogen carbonate (15.47 g). The reaction mixture was stirred at room temperature for 30 mins then allyl bromide (2.39 ml) was added, and stirring continued for a further 36 h at room temperature. The mixture was poured into water (200 ml) and the emerging precipitate was filtered and triturated with boiling methanol to give the desired compound as a beige solid in 50% yield. 1H NMR (360 MHz, DMSO-d6) 5 4.04 (2H, dd, J=6.45 Hz, J=1.84 Hz, OCH2CHCH2), 5.08 (2H, m, OCH2CHCH2), 5.88 (1H, m, OCH2CHCH2), 7.23 (1H, dd, J=12.45 Hz, J=3.00 Hz, 6-H), 7.36 (6H, m, Ph+8-H), 7.81 (1H, d, J=12.45 Hz, 5-H), 11.94 (1H, bs, NH).

Workup

  1. stirringstirring
  2. waitcontinued for a further 36 h at room temperature
  3. filtrationthe emerging precipitate was filtered
  4. customtriturated with boiling methanol

Sources & evidence

ORD record
ord-f912ed0628964bfca4f10d9623fc0d60
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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