Salicylaldehyde → HCID 67050164, compound

HRID 1878052Notes

Reaction equation

HRID 1878052 reaction equation
[H-].[Na+].[CH:3](=O)[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].Cl[CH2:13][C:14]([NH:16][C:17]1[CH:18]=[N:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=1)=[O:15].C[O-].[Na+]>CN(C)C=O.O>[C:23]([C:20]1[N:19]=[CH:18][C:17]([NH:16][C:14]([C:13]2[O:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[CH:3]=2)=[O:15])=[CH:22][CH:21]=1)#[N:24]

Participants

7

Reactant 4

HCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 10942334Sodium MethoxideHCID 44574259HCID 44574259, compound

Product 1

HCID 67050164HCID 67050164, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of sodium hydride (0.184 g, 7.6 mmol) in dry dimethyl formamide (20 mL), a solution of salicylaldehyde (0.947 g, 7.6 mmol) in dry dimethylformamide (20 mL) was added dropwise under stirring. Stirring was continued for 30 minutes, and compound of example 3 (1.5 g, 7.6mmol) was added to the reaction mixture and heated at 80° C. for 2 hours. To this reaction mixture was added a solution of sodium methoxide (0.044 g) and stirred for 1 hour at 80° C. The reaction mixture was cooled, diluted with water and extracted with chloroform (3×100 mL). Chloroform layer was dried over sodium sulfate and concentrated. The crude product was purified using repetitive column chromatography (silica gel, ethyl acetate/petroleum ether followed by chloroform as an eluent) to obtain the title compound.

Workup

  1. stirringStirring
  2. stirringstirred for 1 hour at 80° C
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with chloroform (3×100 mL)
  5. dry with materialChloroform layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-687ad553a71247ca885953ed6b2e97f6
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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