Ethyl Acetate → 9-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo(3,4-C)carbazole-1,3(2H,6H)-dione

HRID 11052Notes

Reaction equation

HRID 11052 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]=3[N:13]([CH2:29][CH2:30][CH2:31][OH:32])[C:12]=2[CH:11]=1.C([O-])(=O)C.[K+].C(OCC)(=O)C>[Pd].CO>[OH:28][C:17]1[CH:16]=[CH:15][C:14]2[N:13]([CH2:29][CH2:30][CH2:31][OH:32])[C:12]3[CH:11]=[C:10]([C:3]4[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=4[O:8][CH3:9])[C:22]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=4[C:20]=3[C:19]=2[CH:18]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 517044Potassium AcetateHCID 9981225HCID 9981225, compound

Product 1

HCID 103645859-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo(3,4-C)carbazole-1,3(2H,6H)-dioneYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (106) (0.20 g, 0.44 mmol) prepared as described in example 59, potassium acetate (0.20 g) and 5% Pd/C in a solution of ethyl acetate (25 ml) and methanol 1:1 (25 mL) under a atmosphere of hydrogen at 60 psi was reacted for 7 h. The catalyst was filtered off and the filtrate concentrated to dryness. The residue was partitioned between ethyl acetate and water and the organic solution was dried, the drying agent was removed and the solution was concentrated to dryness and chromatographed on silica. Elution with ethyl acetate/petroleum ether (2:1) gave 9-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-methoxyphenyl, R10═CH2CH2CH2OH) (107) in a yield of 51% as an orange powder (from THF/petroleum ether), mp 296–300° C. 1H NMR δ [(CD3)2SO] 10.93 (br s, 1H), 9.31 (br s, 1H), 8.38 (d, J=2.4 Hz, 1H), 7.69 (s, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.42 (m, 1H), 7.35 (dd, J=7.5, 1.7 Hz, 1H), 7.13–7.08 (m, 2H), 7.05 (dd, J=7.2, 7.2 Hz, 1H), 4.62 (t, J=4.8 Hz, 1H), 4.48 (t, J=6.8 Hz, 2H), 3.68 (s, 3H), 3.40 (m, 2H), 1.90 (m, 2H). Found: C, 69.29; H, 4.90; N, 6.54. C24H20N2O5 requires C, 69.22; H, 4.84; N, 6.73.

Workup

  1. customwas reacted for 7 h
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate concentrated to dryness
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic solution was dried
  6. customthe drying agent was removed
  7. concentrationthe solution was concentrated to dryness
  8. customchromatographed on silica
  9. washElution with ethyl acetate/petroleum ether (2:1)

Sources & evidence

ORD record
ord-fc288b67d39b4f6c88905d219fdffbcc
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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