Isobutyryl chloride → HCID 69203992, compound

HRID 2252334Notes

Reaction equation

HRID 2252334 reaction equation
[NH:1]([C:3]1[N:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][OH:17])=[CH:5][CH:4]=1)[NH2:2].[C:18](Cl)(=[O:22])[CH:19]([CH3:21])[CH3:20]>>[CH:11]([C:16]1[N:8]2[CH:7]=[C:6]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][O:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:5]=[CH:4][C:3]2=[N:1][N:2]=1)([CH3:12])[CH3:10]

Participants

3

Reactant 2

HCID 62325Isobutyryl chlorideHCID 17974479HCID 17974479, compound

Product 1

HCID 69203992HCID 69203992, compoundYield 77%

Conditions

Temperature
105 °C

Procedure

A mixture of {2-(6-hydrazino-pyridin-3-yloxy)-phenyl]-methanol (231 mg, 1 mmol) and isobutyryl chloride (938 μL, 9 mmol) was heated at 105° C. for 3 hours. The reaction was cooled to ambient temperature and quenched with saturated NaHCO3. The aqueous was extracted with ethyl acetate and the organics combined, dried over sodium sulfate, and concentrated in vacuo to an oil. The residue was purified by flash chromatography (eluting with 2% methanol/ethyl acetate) to give the title compound (136 mg, 39% for two steps).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customquenched with saturated NaHCO3
  3. extractionThe aqueous was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo to an oil
  6. customThe residue was purified by flash chromatography (eluting with 2% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-47a08bf0d0a7405eb1eb45bb1cfc4fbb
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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