5-Chloro-salicylaldehyde → HCID 57750104, compound

HRID 504471Notes

Reaction equation

HRID 504471 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].Cl[C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1.CC([O-])(C)C.[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 124815-Chloro-salicylaldehydeHCID 744042-ChloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 57750104HCID 57750104, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

5-Chloro-2-hydroxy-benzaldehyde (4 g, 25.6 mmol), 2-chloro-pyrimidine (5.4 g, 48 mmol), t-BuOK (3.5 g, 29 mmol) were mixed in DMF (20 mL). Then the mixture was heated for 2 hour at 120° C. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 1N NaOH. Then the organic layer was dried over anhydrous Na2SO4 and concentrated to give title compound as a white solid (Yield: 1.5 g, 25%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N NaOH
  5. dry with materialThen the organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0220dca8ecb44acba5952c1d64fe80dc
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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