Sodium hydride → HCID 75009415, compound

HRID 1160090Notes

Reaction equation

HRID 1160090 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].[CH3:14][O:15][N:16]=[C:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)[CH2:18]Br>CN(C=O)C>[CH3:14][O:15][N:16]=[C:17]([C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[CH2:18][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86049356HCID 86049356, compoundHCID 178515546HCID 178515546, compound

Product 1

HCID 75009415HCID 75009415, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-hydroxyquinoline (242 mg, 1.63 mmol) in DMF (5 mL) was added NaH (125 mg, 3.13 mmol). After 5 minutes of stirring at room temperature, 2-bromo-1-p-tolylethanone O-methyl oxime (400 mg, 1.65 mmol) was added and the mixture was stirred for 30 additional min. The mixture was poured on ice, extracted with Et2O, and dried over MgSO4. Purification by flash chromatography on silica gel (1% MeOH/CH2Cl2) gave a pure product in 28% yield: mp 129-132° C.; 1H NMR 400 MHz (DMSO-d6) δ 2.15 (s, 3H), 4.07 (s, 3H), 5.59 (s, 2H), 6.58 (d, 1H, J=9.2 Hz), 6.98 (d, 2H, J=7.0 Hz), 7.20 (m, 4H), 7.60 (s, 2H), 7.80 (d, 1H, J=8.8 Hz); Elem. anal. found: C, 74.12; H, 5.85; N, 9.00% (calcd for C19H18N2O2: C, 74.49; H, 5.92; N, 9.14%); MS (ESI) m/z 329.00 (MNa+).

Workup

  1. stirringthe mixture was stirred for 30 additional min
  2. additionThe mixture was poured on ice
  3. extractionextracted with Et2O
  4. dry with materialdried over MgSO4
  5. customPurification by flash chromatography on silica gel (1% MeOH/CH2Cl2)
  6. customgave a pure product in 28% yield

Sources & evidence

ORD record
ord-adb5e6c155da4cf2bf5f45e92f177abe
Source dataset
uspto-grants-2010_10
Patent number
US07816352B2

Reaction notes

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