Sodium hydride → 4-(3-(3-Carboxypropanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoic acid

HRID 1801981Notes

Reaction equation

HRID 1801981 reaction equation
[O:1]1CCC[O:3][CH:2]1[CH2:7][CH2:8][C:9]([C:11]1[C:12](=[O:36])[N:13]([CH3:35])[C:14]2[C:19]([C:20]=1[OH:21])=[CH:18][CH:17]=[C:16]([C:22]1[CH:34]=[CH:33][C:25]([C:26]([O:28]C(C)(C)C)=[O:27])=[CH:24][CH:23]=1)[CH:15]=2)=[O:10].C(OC(C1C=CC(C2C=C3C(C(O)=C(C(OC)=O)C(=O)N3C)=CC=2)=CC=1)=O)(C)(C)C.[H-].[Na+]>C1COCC1.CCOC(C)=O>[C:2]([CH2:7][CH2:8][C:9]([C:11]1[C:12](=[O:36])[N:13]([CH3:35])[C:14]2[C:19]([C:20]=1[OH:21])=[CH:18][CH:17]=[C:16]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:33][CH:34]=1)[CH:15]=2)=[O:10])([OH:3])=[O:1]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 67406668HCID 67406668, compoundHCID 67410169Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 547473424-(3-(3-Carboxypropanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(3-(3-(1,3-dioxan-2-yl)propanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoate. Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (452 mg, 1104 μmol) was dissolved in THF (11 mL). Sodium hydride (60% in oil, 442 mg, 11040 μmol) was then added, and the resulting mixture was stirred at room temperature for 1 hour. 2-[2-(1,3-Dioxanyl)]ethylmagnesium bromide in THF (2208 μL, 1104 μmol) was then added dropwise, and the reaction mixture was then stirred for 1 hour. The reaction mixture was diluted with 150 mL of EtOAc, added to a separatory funnel, partitioned with 3 N HCl (aqueous), washed 2 times with 75 mL of brine (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotary evaporation to give initial product. The initial product was purified via flash chromatography (silica gel) to provide the title compound as a beige solid.

Workup

  1. stirringthe reaction mixture was then stirred for 1 hour
  2. additionadded to a separatory funnel
  3. custompartitioned with 3 N HCl (aqueous)
  4. washwashed 2 times with 75 mL of brine (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotary evaporation
  8. customto give initial product
  9. customThe initial product was purified via flash chromatography (silica gel)

Sources & evidence

ORD record
ord-bc68d90f50ae4456bd79147467afbec3
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

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