Water → HCID 58805154, compound

HRID 884458Notes

Reaction equation

HRID 884458 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([OH:14])[C:3]=1[C:15](=[O:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].[C:24]([C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=O)#[N:25].O>CC(C)=O>[OH:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]2[C:3]=1[C:15](=[O:17])[CH:16]=[C:29]([C:28]1[CH:27]=[C:26]([CH:34]=[CH:33][CH:32]=1)[C:24]#[N:25])[O:14]2

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 3084833-Cyanobenzoyl chlorideHCID 58805171HCID 58805171, compound

Product 1

HCID 58805154HCID 58805154, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 1-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)-ethanone (61 mg, 0.257 mmol) and K2CO3 (178 mg, 1.29 mmol) in acetone (3 mL) was added 3-cyanobenzoyl chloride (43 mg, 0.257 mmol). The reaction vessel was sealed and heated to 60° C. for 2 d. After cooling to room temperature, water (about 2 mL) was added, and the mixture was allowed to stir for about 10 min. The contents were transferred to a separatory funnel containing water (5 mL) and extracted with EtOAc (3×15 mL). The organic layer was dried (MgSO4) and concentrated. The concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 30% EtOAc/hexanes to yield 6 mg (7%) of 3-(5-hydroxy-7-morpholin-4-yl-4-oxo-4H-chromen-2-yl)-benzonitrile. Rf=0.33 (50% EtOAc/hexanes).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling to room temperature
  3. customThe contents were transferred to a separatory funnel
  4. extractionextracted with EtOAc (3×15 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-5ea578b0cdad4b85856858d581c8a35c
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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