Water → HCID 21707025, compound

HRID 1594937Notes

Reaction equation

HRID 1594937 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-1cyanonaphthalene (150 mg, 0.65 mmol), and Cs2CO3 (248 mg, 15 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-29a9e8ab08b0433e9942832d39b75954
Source dataset
uspto-grants-2001_09
Patent number
US06284796B1

Reaction notes

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