Hydroquinone → N-(5-acetylpyridin-2-yl)acetamide

HRID 378560

반응식

HRID 378560 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.[CH:12]([O:14]CCCC)=[CH2:13].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.C1(C=CC(O)=CC=1)O>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1)(=[O:14])[CH3:13]

참가 물질

8

반응물 5

HCID 785HydroquinoneHCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 2930972-Acetamido-5-bromopyridine

생성물 1

HCID 10797405N-(5-acetylpyridin-2-yl)acetamide

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

실험 절차

A mixture of 1.07 g (5 mmol) of N-(5-bromo-pyridin-2-yl)-acetamide, 1.00 g (10 mmol) of butyl vinyl ether, 0.245 g (0.8 mmol) of tri-o-tolylphosphine, 0.090 g (0.4 mmol) of palladium acetate, and 1.10 mL (7.9 mmol) of triethylamine in 10 mL of acetonitrile containing 15 mg of hydroquinone was heated at reflux for about 18 hours. The reaction mixture was then cooled, concentrated, and the residue was taken up in 10 mL of 6 M hydrochloric acid and stirred for about 15 minutes. The mixture was then diluted with 40 mL of ethyl acetate, adjusted to pH 8 with 6 M sodium hydroxide, and the aqueous phase was saturated with sodium chloride. The ethyl acetate layer was separated, dried, and concentrated. The residue was chromatographed on silica gel (2:1 ethyl acetate-hexanes), to afford 0.578 g of N-(5-acetyl-pyridin-2-yl)-acetamide as white needles, mp 146-147° C. (recrystallization solvent=1:4 ethanol-hexanes); 1H nmr (deuteriochloroform): δ=8.82 (br s, 1 H), 8.21 (m, 3 H), 2.56 (s, 3 H), 2.22 (s, 3 H); ms (NH3Cl): m/z=179 (MH+).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  3. temperatureThe reaction mixture was then cooled
  4. concentrationconcentrated
  5. additionThe mixture was then diluted with 40 mL of ethyl acetate
  6. customThe ethyl acetate layer was separated
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel (2:1 ethyl acetate-hexanes)
  10. customto afford
  11. custom0.578 g of N-(5-acetyl-pyridin-2-yl)-acetamide as white needles, mp 146-147° C. (recrystallization solvent=1:4 ethanol-hexanes)

출처 및 근거

ORD 기록
ord-0ea8551e0cf74be6a04995f2f6848111
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06031105

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