Water → HCID 58805180, compound

HRID 349706Notes

Reaction equation

HRID 349706 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:34]=[CH:33][C:29]([C:30](Cl)=O)=[CH:28][CH:27]=1)#[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:30]([C:29]1[CH:33]=[CH:34][C:26]([C:24]#[N:25])=[CH:27][CH:28]=1)[O:14]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 801724-Cyanobenzoyl chlorideHCID 58805171HCID 58805171, compound

Product 1

HCID 58805180HCID 58805180, compoundYield 1.5%

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 (45 mg, 0.190 mmol) and K2CO3 (130 mg, 0.948 mmol) in acetone (3 mL) was added 4-cyanobenzoyl chloride 33 mg, 0.20 mmol). The reaction vessel was sealed and heated to 60° C. for 14 h. 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 and extracted with EtOAc (3×15 mL). The organic layer was dried (MgSO4) and concentrated. The concentrate was suspended in 50% EtOAc/hexanes and filtered to yield 1 mg (1%) of 4-(5-hydroxy-7-morpholin-4-yl-4-oxo-4H-chromen-2-yl)-benzonitrile.

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. filtrationfiltered

Sources & evidence

ORD record
ord-377ab462352d484cb679d2fb8db3724d
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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