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

HRID 1904465노트

반응식

HRID 1904465 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b5eb45785ba441ae8c7fd0ffebe11855
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04837235

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