Sodium hydride → HCID 21107320, compound

HRID 1765549Notes

Reaction equation

HRID 1765549 reaction equation
[H-].[Na+].Br[CH2:4][CH:5]([O:18][C:19](=[O:21])[CH3:20])[CH2:6][C:7]1[C:16]([OH:17])=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2>CN(C)C=O>[C:19]([O:18][CH:5]1[CH2:4][O:17][C:16]2[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[CH:11][CH:10]=[CH:9]3)[CH2:6]1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 58883509HCID 58883509, compound2×

Product 1

HCID 21107320HCID 21107320, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60%, 0.27 g, 6.6 mmol) in anhydrous N,N-dimethylformamide (30 ml) was added a pre-cooled solution of acetic acid 1-bromomethyl-2-(6-hydroxyquinolin-5-yl)ethyl ester (intermediate 8) (1.96 g, 6.0 mmol) in 10 ml of N,N-dimethylformamide at 0° C. The reaction mixture was stirred at 0° C. for 1 hr, quenched with water, and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum. Chromatography (10% hexanes-ethyl acetate) afforded 0.89 g (61%) of 2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-yl acetate as a white solid: mp 125.4–127° C. MS ESI m/z 244 [M+H]+. Elemental Analysis for C14H13NO3: Calculated: C, 69.12; H, 5.39; N, 5.76. Found: C, 69.12; H, 5.48; N, 5.64.

Workup

  1. customquenched with water
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-555371ba56fb4838a971619182b24db1
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

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