N-Iodosuccinimide → HCID 86677824, compound

HRID 1499908Notes

Reaction equation

HRID 1499908 reaction equation
[C:1]([C:4]1[C:11]([OH:12])=[CH:10][C:7]([C:8]#[N:9])=[C:6]([CH3:13])[CH:5]=1)(=[O:3])[CH3:2].[I:14]N1C(=O)CCC1=O>C(O)(=O)C.C(OCC)(=O)C>[C:1]([C:4]1[CH:5]=[C:6]([CH3:13])[C:7]([C:8]#[N:9])=[C:10]([I:14])[C:11]=1[OH:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 86677823HCID 86677823, compound

Product 1

HCID 86677824HCID 86677824, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The 4-acetyl-5-hydroxy-2-methylbenzonitrile (6.7 g, 38 mmol) was dissolved in acetic acid (80 mL) and the N-Iodosuccinimide (10.0 g, 46 mmol) was added. The reaction was heated to 80° C. in an oil bath and monitored by LC/MS. After heating for 4 hrs the reaction was complete. This was allowed to cool and was concentrated in vacuo to give a dark oil. The oil was taken up in ethyl acetate and washed with water, sodium bicarbonate (3×, until remained slightly basic), brine, dried over magnesium sulfate and concentrated to give the crude product as a dark oil. The product was purified by FCC on silica gel eluting hexane:ethyl acetate gradient to give 4-acetyl-3-hydroxy-2-iodo-6-methylbenzonitrile as pale yellow solid (7.2 g, 62%). LCMS calculated for C10H9INO2(M+H)+: m/z=301.9; found: 301.9.

Workup

  1. temperatureAfter heating for 4 hrs the reaction
  2. temperatureto cool
  3. concentrationwas concentrated in vacuo
  4. customto give a dark oil
  5. washwashed with water, sodium bicarbonate (3×
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give the crude product as a dark oil
  9. customThe product was purified by FCC on silica gel
  10. washeluting hexane

Sources & evidence

ORD record
ord-afd00ae3d5ae495c9f56cb112a8f88b7
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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