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Trifluoroacetic acid → 6-Methyl-5-nitro-1H-isochromen-1-one

HRID 1161180
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HRID 1161180 반응식
[N+:1]([C:4]1[C:13]([CH2:14]C(OC(C)(C)C)=O)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][O:8][C:9]2=[O:22])([O-:3])=[O:2].FC(F)(F)C(O)=O.N1C2C(=CC=CC=2)C=CC=1>C(OC(=O)C)C>[CH3:14][C:13]1[C:4]([N+:1]([O-:3])=[O:2])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:22])[O:8][CH:7]=[CH:6]2
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 7047QuinolineHCID 59515864tert-butyl 2-(5-nitro-1-oxo-1H-isochromen-6-yl)acetate

생성물 1

HCID 595157846-Methyl-5-nitro-1H-isochromen-1-one

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

A microwave vial was charged with tert-butyl 2-(5-nitro-1-oxo-1H-isochromen-6-yl)acetate (800.0 mg, 0.002620 mol), trifluoroacetic Acid (2 mL, 0.02 mol) and subjected to microwave at 100° C. for 20 minutes. The starting material became converted into the corresponding acid. TFA was removed under reduced pressure and the residue was again taken a microwave tube and quinoline (2 mL, 0.02 mol) was added and heated at 120° C. for 20 minutes. The reaction went to completion and ethylacetate (50 mL) was added and washed with 10 mL of 6N HCl. The HCl layer was extracted with ethyl acetate (50 mL) and the combined organic layers were washed with water, brine and dried. The solvent was removed and the brown solid residue was purified by flash chromatography to yield the pure product as a white solid. MS m/z=206.4 (M+H) 1H-NMR (400 MHz, DMSO-d6) δ 8.29 (d, J=8.19 Hz, 1H), 7.71-7.69 (m, 2H), 6.57 (d, J=6.02 Hz, 1H), 2.45 (s, 3H).

후처리

  1. customTFA was removed under reduced pressure
  2. additionwas added
  3. washwashed with 10 mL of 6N HCl
  4. extractionThe HCl layer was extracted with ethyl acetate (50 mL)
  5. washthe combined organic layers were washed with water, brine
  6. customdried
  7. customThe solvent was removed
  8. customthe brown solid residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-53fe8b51eb2d43fda909fdbb9d8cc233
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816371B2

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