Hydrochloric Acid → HCID 66668615, compound

HRID 1617629Notes

Reaction equation

HRID 1617629 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9](=[O:24])[CH2:10][CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.Cl>O1CCOCC1>[C:18]1([CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][C:9]([C:6]2[CH:5]=[CH:4][C:3](=[O:2])[NH:8][CH:7]=2)=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67015564HCID 67015564, compound

Product 1

HCID 66668615HCID 66668615, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(6-methoxy-pyridin-3-yl)-3,3-diphenyl-propan-1-one (468 mg) in 1,4-dioxane (25 ml) was added concentrated aqueous HCl (2.69 ml). The mixture was stirred for 2 h at 100° C. After cooling to room temperature, the mixture was poured into ice and extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 4:1) to give the title compound (127 mg) as a colorless solid, MS (ESI−): m/z=302.0 [M−H]−.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured into ice
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 4:1)

Sources & evidence

ORD record
ord-93f6910099484dd8816dbd1a1b4a940b
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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