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

HRID 1904465Notes

Reaction equation

HRID 1904465 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b5eb45785ba441ae8c7fd0ffebe11855
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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