Methyl bromoacetate → HCID 10617376, compound

HRID 977174Notes

Reaction equation

HRID 977174 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.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[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

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 516892Sodium BicarbonateHCID 546974683-Phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one

Product 1

HCID 10617376HCID 10617376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (0.5 g) in DMF was stirred for 14 h with methyl bromoacetate (206 μl) and sodium bicarbonate (1.55 g). The reaction mixture was then partitioned between water and ethyl acetate. The aqueous phase was extracted with two further portions of ethyl acetate. The combined organic phases were washed with brine (3×), dried (MgSO4) and the solvent was removed in vacuo to give the crude product which was recrystallised from ethyl acetate-hexane to give the title compound, 208 mg; mp 188°-191° C. (ethyl acetate-hexanes); Found: C, 63.27; H, 4.24; N, 4.07. C18H14ClNO4 requires C, 62.89; H, 4.11; N, 4.07%; δ (360 MHz, DMSO-d6) 3.55 (3H, s, CO2CH3), 4.19 (2H, s, CH2CO2), 7.28 (1H, dd, J=2.6, 8.7 Hz, 6-H), 7.35-7.40 (6H, m, aromatics), 8.01 (1H, d, J=8.7 Hz, 5-H), 11.92 (1H, s, NH); m/z CI+ 344 (M+).

Workup

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted with two further portions of ethyl acetate
  3. washThe combined organic phases were washed with brine (3×)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customto give the crude product which
  7. customwas recrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8da0dfe4af8445cb92b81142bfe1e95c
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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