Water → HCID 21707025, compound

HRID 1384184Notes

Reaction equation

HRID 1384184 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](C#N)=[CH:16][CH:15]=[CH:14]2.C([O-])([O-])=O.[Cs+].[Cs+].O.[CH3:30][N:31](C=O)C>>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:30]#[N:31])[CH:20]=[CH:19]2)=[O:5]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6998SalicylaldehydeHCID 10796Cesium carbonateHCID 217069836-Bromonaphthalene-1-carbonitrile

Product 1

HCID 21707025HCID 21707025, compound

Procedure

A solution of 2-hydroxybenzaldehyde (72 mg, 0.59 mmol), 6-bromo-1-cyanonaphthalene (150 mg, 0.65 mmol), and Cs2CO3 (248 mg, 0.76 mmol) in DMF (10 mL) was heated at 90° C. for 2 days, treated with water and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated, and the crude product was purified by column chromatography with 10% ethyl acetate/hexane to provide 40 mg of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customthe crude product was purified by column chromatography with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e5695dd359be477190282ab59aba3072
Source dataset
uspto-grants-2001_07
Patent number
US06258822B1

Reaction notes

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