Pyridine → HCID 10831621, compound

HRID 1379905Notes

Reaction equation

HRID 1379905 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.C(OC(=O)C)(=O)C>CO.CC(N(C)C)=O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6](=[O:8])[C:5]2=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6115AnilineHCID 7918Acetic AnhydrideHCID 152633775-Iodo-2-benzofuran-1,3-dione

Product 1

HCID 10831621HCID 10831621, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

As described above, 4-iodophthalic anhydride (2.0 g, 7.3 mmol), aniline (665 μL, 7.3 mmol), pyridine (2.1 mL, 25.5 mmol) and DMAc (10 mL) were heated at 80° C. for 2 hours, followed by continued heating in the presence of acetic anhydride (2.75 mL, 29.2 mmol) for 16 hours. MeOH (5 mL) was added to the warm solution which was then cooled to room temperature. The crystalline solid was removed by filtration, washed with MeOH and dried in vacuo to give 1.96 g (77%) product. The filtrate was concentrated and cooled to 0° C. to afford another 300 mg (11%) product. Total yield 88% mp 178°-179° C., 1H NMR (CDCl3) δ8.27 (d, J=1.0 Hz, 1), 8.13 (dd, J=7.5, 1.0 Hz, 1), 7.65 (d, J=7.9 Hz, 1), 7.49 (m, 2), 7.40 (m, 3). 13C NMR (CDCl3) {1H} δ166.6, 165.7, 143.3, 133.1, 132.8, 131.5, 131.0, 129.1, 128.2, 126.4, 124.9, 101.1. Combustion analysis calculated for C14H8INO2 : C, 48.16; H, 2.31; N, 4.01. Found: C, 47.81; H, 2.39; N, 3.95.

Workup

  1. temperaturewas then cooled to room temperature
  2. customThe crystalline solid was removed by filtration
  3. washwashed with MeOH
  4. customdried in vacuo

Sources & evidence

ORD record
ord-16927af02a5e466b9022dc695112037c
Source dataset
uspto-grants-1997_09
Patent number
US05672750

Reaction notes

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