Sodium hydride → HCID 70051652, compound

HRID 465364Notes

Reaction equation

HRID 465364 reaction equation
[H-].[Na+].O[C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]([C:18]#[N:19])[C:13](=[O:17])[NH:14][C:15]=2[CH3:16])[CH:7]=[CH:8][CH:9]=1.BrCCC[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C=O)C>[C:24]([C:4]1[C:5]([O:17][CH2:13][CH2:12][CH3:11])=[C:6]([C:10]2[CH2:11][CH:12]([C:18]#[N:19])[C:13](=[O:17])[NH:14][C:15]=2[CH3:16])[CH:7]=[CH:8][CH:9]=1)([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 15682645HCID 15682645, compound

Product 1

HCID 70051652HCID 70051652, compoundYield 116.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A dispersion of 337 mg (14.0 mmol) of 60% sodium hydride in mineral oil and 5 ml of DMF is treated, dropwise, with a solution of 1.60 g (7.0 mmol) of 5-(3-hydroxyphenyl)6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile. The reaction is stirred 30 min at RT, then cooled in an ice bath and 1.36 g (7.0 mmol) of ethyl 4-bromobutyrate in 5 ml of DMF is added dropwise. The reaction is allowed to slowly come to RT and stirred over night. The mixture is concentrated under vacuum, the residue is taken up in 80 ml of water, extracted with EtOAc, acidified to pH=5 with IN HCl, and the aqueous phase extracted with EtOAc (4×80 ml). The EtOAc is dried (MgSO4) and the solvent removed to leave a light yellow solid. This solid is triturated with hot ether and filtered to give 1.40 g of 5-(3-carboethoxy-propyloxyphenyl)-6-methyl-2-oxo-1,3-dihydro-3-pyridinecarbonitrile as a pale yellow solid, m.p. 168°-169° C. 1H-NMR (d6 -DMSO): δ1.20 (t,3H); 1.95 (m,2H); 2.15 (s,3H); 2.50 (t,2H); 4.03 (q,2H); 4.05 (t,2H); 6.95 (m,3H); 7.30 (m,1H); 8.10 (s,1H).

Workup

  1. temperaturecooled in an ice bath
  2. customto slowly come to RT
  3. stirringstirred over night
  4. concentrationThe mixture is concentrated under vacuum
  5. extractionextracted with EtOAc
  6. extractionthe aqueous phase extracted with EtOAc (4×80 ml)
  7. dry with materialThe EtOAc is dried (MgSO4)
  8. customthe solvent removed
  9. customto leave a light yellow solid
  10. customThis solid is triturated with hot ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-af88e40d7061473ea549f3f0c108ad31
Source dataset
uspto-grants-1992_10
Patent number
US05153209

Reaction notes

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