9-Benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxamide → Carbazole

HRID 567354

반응식

HRID 567354 반응식
C([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH:16](C(N)=O)[C:15]=2[C:14]2[C:9]1=[C:10](C)[CH:11]=[CH:12][C:13]=2OC)C1C=CC=CC=1>CCOCCOCCO.[Pd]>[CH:10]1[C:9]2[NH:8][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

참가 물질

4

반응물 1

HCID 227406579-Benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxamide

생성물 1

HCID 6854Carbazole수율 43%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8146Diethylene Glycol Monoethyl Ether용매

실험 절차

A solution of 0.805 g of 9-benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxamide in 24 ml of carbitol was treated with 1.1 g of 5% palladium on carbon and was refluxed for 6 hours open to the air. After cooling, the solution was filtered thourough a pad of celite and the pad was washed with ethyl acetate. The filtrates were diluted with ether and washed four times with water and dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel using methanol/0-4% in dichloromethane to afford 0.166 g (28%) of debenzylated carbazole. ESIMS m/e 255 (M++1), 253 (M+−1) NMR (300 MHz, CDCl3): δ 8.13 (br, 1H); 7.51 (d, J=8.1, 1H); 7.40 (t, J=7.6, 1H); 7.32 (d, J=7.2, 1H); 7.18 (d, J=7.8, 1H); 6.60 (d, J=8.0, 1H); 5.68 (br, 2H); 3.99 (s, 3H); 2.50 (s 3H).

후처리

  1. temperaturewas refluxed for 6 hours open to the air
  2. temperatureAfter cooling
  3. filtrationthe solution was filtered thourough a pad of celite
  4. washthe pad was washed with ethyl acetate
  5. additionThe filtrates were diluted with ether
  6. washwashed four times with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-c58f4a6e4af64709baa4a812df2eeb32
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177440B1

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