Acetone → HCID 21541262, compound

HRID 1926303Notes

Reaction equation

HRID 1926303 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](Cl)=[O:11])=[CH:5][CH:4]=1.[CH:13]([NH2:15])=[O:14].N1C=CC=CC=1.C[C:23](C)=[O:24]>CCOC(C)=O>[CH:13]([NH:15][C:10](=[O:11])[CH2:9][C:6]1[CH:5]=[CH:4][CH:3]=[C:8]([O:24][CH3:23])[CH:7]=1)=[O:14]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 713FormamideHCID 1049PyridineHCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 21541262HCID 21541262, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of (4-methoxyphenyl)acetyl chloride (0.500 g, 2.71 mmol) in acetone (1.0 mL) at 0° C. was added a solution of formamide (0.28 mL, 7.0 mmol) and pyridine (0.28 mL, 3.5 mmol) in acetone (1.0 mL). The resulting solution was stirred at 0° C. for 30 min and then overnight at rt. The reaction mixture was diluted with EtOAc and washed with 1M HCl, sat. NaHCO3 solution, brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by column chromatography eluting with 1% MeOH in DCM yielding the title compound as an off-white solid. MS (ES+): m/z=194.11 [MH+]. HPLC: tR=2.57 min (ZQ3, polar—5 min).

Workup

  1. customovernight
  2. customat rt
  3. washwashed with 1M HCl, sat. NaHCO3 solution, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by column chromatography
  8. washeluting with 1% MeOH in DCM yielding the title compound as an off-white solid
  9. custom5 min

Sources & evidence

ORD record
ord-7c852c86dcf4424092556dcb747bfbf6
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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