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

HRID 567354

Reaction equation

HRID 567354 reaction equation
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

Participants

4

Reactant 1

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

Product 1

HCID 6854CarbazoleYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8146Diethylene Glycol Monoethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c58f4a6e4af64709baa4a812df2eeb32
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Linked notes

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