Hydrochloric Acid → Methyl 3-methoxy-4-(1-ethyl-5-nitroindol-3-ylmethyl)benzoate

HRID 1904465ノート

反応式

HRID 1904465 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=2)[NH:16][CH:15]=1)[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].I[CH2:29][CH3:30].Cl>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=2)[N:16]([CH2:29][CH3:30])[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 114732633-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole

生成物 1

HCID 20038743Methyl 3-methoxy-4-(1-ethyl-5-nitroindol-3-ylmethyl)benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Methyl 3-methoxy-4-(5-nitroindol-3-ylmethyl)benzoate (F) (5.30 g) was added to a stirred suspension of oil-free sodium hydride (0.424 g) in dry N,N-dimethylformamide (25 ml), under an atmosphere of nitrogen. The dark-red solution was stirred for 15 minutes, and iodoethane (3.04 g) was added. The mixture was stirred for 30 minutes, and was poured into 1M hydrochloric acid (75 ml). The mixture obtained was extracted wih ethyl acetate (2×50 ml). The combined extracts were washed with brine (25 ml), then dried (MgSO4), and evaporated. The yellow oil obtained was purified by flash chromatography on silica gel (600 ml), eluting with 70:30 v/v hexane:ethyl acetate, to give methyl 3-methoxy-4-(1-ethyl-5-nitroindol-3-ylmethyl)benzoate (G) as a yellow oil, which was crystallized from methylene chloride/hexane to give yellow needles (4.88 g, 82%); mp 129°-30° C.; 1.34(t, 3H, CH2CH3), 3.83(s, 3H, CO.OCH3), 3.92(s, 3H, OCH3), 4.11 (s, 2H, CH2Ar), 4.23(q, 2H, CH2CH3), 7.27(d, 1H), 7.48(m, 2H), 7.64(d, 1H), 7.99(dd, 1H, H6 -indole), 8.49(d, 1H, H4 -indole).

後処理

  1. stirringThe mixture was stirred for 30 minutes
  2. customThe mixture obtained
  3. extractionwas extracted wih ethyl acetate (2×50 ml)
  4. washThe combined extracts were washed with brine (25 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe yellow oil obtained
  8. customwas purified by flash chromatography on silica gel (600 ml)
  9. washeluting with 70:30 v/v hexane

出典と根拠

ORDレコード
ord-b5eb45785ba441ae8c7fd0ffebe11855
出典データセット
uspto-grants-1989_06
特許番号
US04837235

反応ノート

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