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

HRID 11102

反応式

HRID 11102 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2074e4d1b268405a81592841c2097642
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

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