Hydrochloric Acid → 4-(2-chlorophenyl)-9-hydroxy-6-(3-methoxypropyl)-1H-furo[3,4-c]carbazole-1,3(6H)-dione

HRID 11102

반응식

HRID 11102 반응식
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:14]3[C:25](=[O:29])N[C:27](=[O:28])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:30])[CH:8]=[CH:7][C:6]1=2.[CH3:31][O-:32].[Na+].Cl.C[OH:36]>O1CCOCC1>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:15]1[C:14]2[C:25](=[O:36])[O:29][C:27](=[O:28])[C:13]=2[C:12]2[C:11]3[CH:10]=[C:9]([OH:30])[CH:8]=[CH:7][C:6]=3[N:5]([CH2:4][CH2:3][CH2:2][O:32][CH3:31])[C:17]=2[CH:16]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 219805126-(3-Bromopropyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

생성물 1

HCID 219805254-(2-chlorophenyl)-9-hydroxy-6-(3-methoxypropyl)-1H-furo[3,4-c]carbazole-1,3(6H)-dione

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of the bromide (58) (50 mg, 0.103 mmol) prepared as described in example 172 and sodium methoxide (35.2 mg, 0.65 mmol) in methanol (0.5 mL) and p-dioxane (8 mL) was refluxed for 3 h. The solution was acidified with 2N HCl, extracted with ethyl acetate and the organic layer was dried, the drying agent was removed and the solution was concentrated to dryness and chromatographed on silica. Elution with ethyl acetate gave the anhydride, 4-(2-chlorophenyl)-9-hydroxy-6-(3-methoxypropyl)-1H-furo[3,4-c]carbazole-1,3(6H)-dione as an orange powder. 1H NMR δ [(CD3)2SO] 9.57 (br, 1H), 8.24 (d, J=2.3 Hz, 1H), 8.00 (s, 1H), 7.66–7.61 (m, 2H), 7.58–7.48 (m, 3H), 7.22 (dd, J=9.0, 2.3 Hz, 1H), 4.56 (t, J=6.7 Hz, 2H), 3.22 (t, J=6.0 Hz, 2H), 3.13 (s, 3H), 2.02 (m, 2H). The product was added to molten ammonium acetate (10 g) at 140° C. and the mixture was warmed at this temperature for 3 h. Water was added and the resultant precipitate was filtered off, adsorbed onto silica from a THF solution, and chromatographed. Elution with ethyl acetate/petroleum ether (1:1) gave (132) (32 mg, 71%) an orange powder, mp 260–262° C. 1H NMR δ [(CD3)2SO] 11.07 (br s, 1H), 9.42 (br s, 1H), 8.39 (d, J=2.4 Hz, 1H), 7.69 (s, 1H), 7.60–7.44 (m, 5H), 7.15 (dd, J=8.8, 2.4 Hz, 1H), 4.49 (t, J=6.6 Hz, 2H), 3.22 (t, J=6.0 Hz, 2H), 3.13 (s, 3H), 1.99 (m, 2H). FABMS found [M+H]+: 437.1088, 435.1090. C24H20ClN2O4 requires 437.1082, 435.1112.

후처리

  1. temperaturewas refluxed for 3 h
  2. extractionextracted with ethyl acetate
  3. customthe organic layer was dried
  4. customthe drying agent was removed
  5. concentrationthe solution was concentrated to dryness
  6. customchromatographed on silica
  7. washElution with ethyl acetate

출처 및 근거

ORD 기록
ord-2074e4d1b268405a81592841c2097642
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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