Sodium hydride → HCID 59354779, compound

HRID 655361Notes

Reaction equation

HRID 655361 reaction equation
[CH3:1][C:2]([NH:8][C:9](=[O:29])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:13][CH:12]=1)([CH3:7])[C:3]([O:5]C)=O.[H-].[Na+]>CN(C=O)C>[OH:5][C:3]1[C:2]([CH3:7])([CH3:1])[NH:8][C:9](=[O:29])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 59354798HCID 59354798, compound

Product 1

HCID 59354779HCID 59354779, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 2-methyl-2-(2-(4-(quinolin-2-ylmethoxy)phenyl)acetamido)propanoate (5.0 g, 0.01 mol) in DMF (100 mL) was added NaH (913 mg, 0.03 mmol) at 0° C. under an inert atmosphere. The reaction mixture was then stirred for 2 h, diluted with ice water and then extracted with EtOAc (2×200 mL). The combined organic layers were washed with water and brine, and then dried over Na2SO4 and concentrated in vacuo to afford 4-hydroxy-5,5-dimethyl-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-one (2.0 g, 44%) as a white solid.

Workup

  1. extractionextracted with EtOAc (2×200 mL)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cf36f8645c24b1d88dafeba3e54b820
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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