Acetic Acid → HCID 178463257, compound

HRID 1968163Notes

Reaction equation

HRID 1968163 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:11].[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[CH3:20])=[CH:15][CH:14]=1.S([O-])([O-])(=O)=O.[Mg+2].C(O)(=O)C>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:18]=[CH:17][C:16](/[C:19](=[N:1]/[C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][O:5][C:6]3=[O:11])/[CH3:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 98284'-FluoroacetophenoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 178463257HCID 178463257, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-aminoisobenzofuran-1(3H)-one (1 g, 6.7 mmol) and 1-(4-fluorophenyl)ethanone (1.4 g, 10.1 mmol) in toluene (35 mL) was added anhydrous magnesium sulfate (8.8 g, 73.7 mmol) and acetic acid (0.2 mL) at room temperature under N2. The reaction mixture was then stirred at 120° C. for 36 hr. The reaction mixture was cooled to 90° C. and filtered. After filter cake was washed with acetonitrile, the filtrates were combined and evaporated to dryness to obtain yellow solid, which was washed by petroleum ether to obtain the title compound as a white solid (1.58 g, yield 88%). LC-MS (ESI) m/z: 270 (M+1)+ 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.30 (s, 3H), 5.16 (s, 2H), 7.00-7.02 (d, J=7.6 Hz, 1H), 7.13-7.18 (m, 2H), 7.51-7.56 (t, J=7.6 Hz, 1H), 7.66-7.69 (d, J=7.6 Hz, 1H), 7.99-8.03 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to 90° C.
  2. filtrationfiltered
  3. filtrationAfter filter cake
  4. washwas washed with acetonitrile
  5. customevaporated to dryness
  6. customto obtain yellow solid, which
  7. washwas washed by petroleum ether

Sources & evidence

ORD record
ord-49e283a3c02f44bc86bfe6b11bcb0689
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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