Dimethylformamide → HCID 70058562, compound

HRID 728906Notes

Reaction equation

HRID 728906 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.Br[CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].CN(C=[O:33])C>>[C:24]([CH2:23][CH2:22][CH2:21][O:33][C:7]1[CH:8]=[CH:9][CH:4]=[CH:5][C:6]=1[C:10]1[CH2:11][CH:12]([C:18]#[N:19])[C:13](=[O:17])[NH:14][C:15]=1[CH3:16])([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 15682645HCID 15682645, compound

Product 1

HCID 70058562HCID 70058562, compound

Procedure

A dispersion of 337 mg (14.0 mmol) of 60% sodium hydride in mineral oil and5 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. Thereaction 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 1N 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-carboethoxypropyloxyphenyl)-6-methyl-2-oxo-1,3-dihydro-3 -pyridinecarbonitrile as a pale yellow solid, m.p. 168°-169°C. 1H-NMR (d6 -DMSO): δ 1.20 (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-d2d630dcca744c1da6616c805bcde5ba
Source dataset
uspto-grants-1991_09
Patent number
US05051431

Reaction notes

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