Dimethylformamide → HCID 136188863, compound

HRID 1868913Notes

Reaction equation

HRID 1868913 reaction equation
C(=N[OH:9])C1C=CC=CC=1.CN(C=O)C.[H-].[Na+].O1CCOCC1.[C:23]([C:25]([C:28]1[C:33]([C:34]#[C:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:32][CH:31]=[CH:30][N:29]=1)([CH3:27])[CH3:26])#[N:24]>>[OH:9][C:34]1[C:33]2[CH:32]=[CH:31][CH:30]=[N:29][C:28]=2[C:25]([CH3:27])([CH3:26])[C:23](=[NH:24])[C:35]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 12143(Z)-Benzaldehyde oximeHCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 57983363HCID 57983363, compound

Product 1

HCID 136188863HCID 136188863, compound

Procedure

A solution of benzaldehyde oxime (0.6 g, 5 mmol) in dry DMF (10 mL, 129 mmol) was added to a stirred suspension of 60% NaH (0.2 g, 5 mmol) in dry 1,4-dioxane (10 mL, 117 mmol) under a nitrogen atmosphere at room temperature. After 0.5 hours, a solution of the ethyl 3-(2-(2-cyanopropan-2-yl)pyridin-3-yl)propiolate (0.98 g, 4 mmol) in dry DMF (10 mL, 129 mmol) was added, and the solution was stirred for 30 minutes. The solvent was removed under vacuum, and water was added to the residue. The product was extracted with EtOAc. The organic layer was washed with water (3×) and then with saturated NH4Cl and brine (3× each) and dried over MgSO4. The resulting mixture was concentrated in vacuo to give a light-yellow crystalline solid/yellow oil. The yellow residue was washed with hexane providing the product as a yellow solid which was filtered off (0.65 g, 62%). MS (m/z)=261 (M+H)+. Calculated for C14H16N2O3 260.3.

Workup

  1. customThe solvent was removed under vacuum, and water
  2. additionwas added to the residue
  3. extractionThe product was extracted with EtOAc
  4. washThe organic layer was washed with water (3×)
  5. dry with materialwith saturated NH4Cl and brine (3× each) and dried over MgSO4
  6. concentrationThe resulting mixture was concentrated in vacuo
  7. customto give a light-yellow crystalline solid/yellow oil
  8. washThe yellow residue was washed with hexane providing the product as a yellow solid which
  9. filtrationwas filtered off (0.65 g, 62%)

Sources & evidence

ORD record
ord-10dd2ef5b0874e219f28eb36d442d6f5
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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