Methyl Acrylate → HCID 18926558, compound

HRID 1600178Notes

Reaction equation

HRID 1600178 reaction equation
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[N+:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)([O-:15])=[O:14].[C:32]([O:36][CH3:37])(=[O:35])[CH:33]=[CH2:34]>O1CCOCC1>[N+:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:34][CH2:33][C:32]([O:36][CH3:37])=[O:35])[CH:20]=[C:19]2[CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 18926554HCID 18926554, compound

Product 1

HCID 18926558HCID 18926558, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Benzyltrimethylammonium hydroxide (0.8 ml of 40% solution in methanol) was added to a stirred mixture of 5-nitro-3-(3-pyridylmethyl)-1H-indole (7.34 g) and methyl acrylate (3.0 g) in dioxan (140 ml) and the resulting solution was stirred for 75 minutes and then evaporated. The residue was partitioned between water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. The organic layers were combined, washed with water and dried (Na2SO4). Evaporation of the solvent gave a solid which was crystallised from ethyl acetate/hexane to give the title compound (7.33 g), m.p. 101°-102° C. Found: C,63.85; H,4.86; N,12.37. C18H17N3O4 requires: C,63.71; H,5.05; N,12.38%.

Workup

  1. customevaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave a solid which
  9. customwas crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6c8d085adccf439a9882d668890cc419
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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