Boron tribromide → Diethyl (6-hydroxy-3-quinolyl)methylacetamidomalonate

HRID 1684413Notes

Reaction equation

HRID 1684413 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([CH2:13][CH2:14][C:15]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])=[CH:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([CH2:13][CH2:14][C:15]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])=[CH:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57184951Diethyl (6-methoxy-3-quinolyl)methylacetamidomalonate

Product 1

HCID 57234501Diethyl (6-hydroxy-3-quinolyl)methylacetamidomalonateYield 11.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.39 g (1 mmol) of diethyl (6-methoxy-3-quinolyl)methylacetamidomalonate in 10 mL of dry methylene chloride was added dropwise at -70° C. a 1M solution of boron tribromide in methylene chloride. The reaction temperature was gradually raised to room temperature while stirring overnight. Then, the reaction mixture was poured into ice water and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel, using 1:1 ethyl acetate/methylene chloride and then ethyl acetate as eluents, to give 43 mg (11.5%) of the desired product as a solid. TLC Rf =0.46 (ethyl acetate); NMR (CDCl3) δ 8.4 (1H, bs), 7.95 (1H, d), 7.7 (1H, bs), 7.35 (1H, dd), 7.1 (1H, d), 6.8 (1H, bs), 4.25 (4H, m), 3.8 (2H, bs), 2.0 (3H, s), 1.3 (6H, m); IR (KBr) ν 3700-2800, 1740, 1660, 1645, 1620, 1500 cm-1. The product has the structural formula: ##STR88##

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0615c483333d4d3f8de357519332168a
Source dataset
uspto-grants-1997_06
Patent number
US05639885

Reaction notes

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