Hydrochloric Acid → 9-[(3,5-Dimethylphenyl)methyl]-4-hydroxy-5-carbamoyl carbazole

HRID 51408Notes

Reaction equation

HRID 51408 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][C:15]=3[C:24]([O:26]C)=O)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl.[OH-].[NH4+:30]>C1COCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][C:15]=3[C:24](=[O:26])[NH2:30])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 22738922HCID 22738922, compound

Product 1

HCID 227390959-[(3,5-Dimethylphenyl)methyl]-4-hydroxy-5-carbamoyl carbazoleYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the 9-[(3,5-dimethylphenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole (200 mg, 0.55 mM) in 10 mL THF and 30 mL concentrated aqueous ammonium hydroxide was sonicated for 4 days at 40-50° C. The mixture was diluted with ethyl acetate and acidified to pH 2.5 with 5 N HCl. The aqueous layer was extracted three times with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (elution with gradient hexanes/ethyl acetate) to afford 90 mg (47%) of the 9-[(3,5-dimethylphenyl)methyl]-4-hydroxy-5-carbamoyl carbazole as an off-white solid. 1H NMR (DMSO-d6) δ10.5 (s, 1H), 8.6 (s, 1H), 8.4 (s, 1H), 7.75 (d, 1H, J=8 Hz), 7.45 (m, 2H), 7.3 (t, 1H, J=8 Hz), 7.1 (d, 1H, J=8 Hz), 6.85 (s, 1H), 6.7 (s, 2H), 6.6 (d, 1H, J=8 Hz), 5.6 (s, 2H), and 2.2 (s, 6H). IR (KBr, cm−1) 3417, 3198, 3113, 3063, 1631, 1601, 1562, 1438, 1332, 1263, 1217, 781, and 773. MS (ES) m/e 343, 345.

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (elution with gradient hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e3b0e9b74ba34939a193e156c8f65c90
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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