Sodium hydride → HCID 67181313, compound

HRID 2400214Notes

Reaction equation

HRID 2400214 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[C:6](=[O:11])[NH:7][CH:8]=[CH:9][CH:10]=1.[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>C1COCC1>[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:3][CH2:4][C:5]2[C:6](=[O:11])[NH:7][CH:8]=[CH:9][CH:10]=2)=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 678794-Fluorobenzoyl chlorideHCID 106304823-(Hydroxymethyl)pyridin-2(1H)-one

Product 1

HCID 67181313HCID 67181313, compoundYield 14.94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In Example 2, 0.0725 g of 60% sodium hydride (NaH) was dispersed in mineral oil (1.60 mmol) and was suspended in 40 mL of THF in a 100 mL RBF under the presence of argon gas. Then, 0.2003 g (1.60 mmol) of 3-(hydroxymethyl)pyridine-2(1H)-one was added slowly and the solution stirred for 30 min with gentle heating before 0.250 mL (2.08 mmol) of 4-fluorobenzoyl chloride was added dropwise. The reaction was allowed to stir with gentle heating and for 48 hours. The reaction was quenched with the addition of 20 mL of water. The reaction was washed with ethyl acetate (4×20 mL) and the organic layers combined. The organic layer was washed with brine (3×20 mL) and dried over MgSO4. The solvent was evaporated in vacuo to produce a white solid. The product was purified by crystallization from toluene. The yield of the reaction was 0.0590 g (14.94% yield). MP: 170-173° C. IR (cm−1): 3415.21 (m, broad), υ (O—H), 3125.47 (m, broad), υ (N—H), 1716.90 (m), υ (C═O), 1614.44 (m), (C═C aromatic). 1H NMR (DMSO-d6, 500 MHz) δ: 5.13 (s, 2H), 6.23 (t, J=6.6 Hz, 1H), 7.37 (t, J=8.9 Hz, 2H), 7.41 (dd, J=4.5, 2.1 Hz, 1H), 7.59 (dd, J=4.7, 2.1 Hz, 1H), 8.06 (t, J=7.7 Hz, 2H), 11.78 (s, 1H).

Workup

  1. additionwas added dropwise
  2. stirringto stir
  3. temperaturewith gentle heating and for 48 hours
  4. customThe reaction was quenched with the addition of 20 mL of water
  5. washThe reaction was washed with ethyl acetate (4×20 mL)
  6. washThe organic layer was washed with brine (3×20 mL)
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated in vacuo
  9. customto produce a white solid
  10. customThe product was purified by crystallization from toluene

Sources & evidence

ORD record
ord-c8b3f275914b4ee3a7a8c9606561e604
Source dataset
uspto-grants-2014_08
Patent number
US08795630B2

Reaction notes

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