Methyl Acrylate → HCID 18926604, compound

HRID 1600180Notes

Reaction equation

HRID 1600180 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[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)([O-:15])=[O:14].[C:31]([O:35][CH3:36])(=[O:34])[CH:32]=[CH2:33].CC(C)([O-])C.[K+]>O1CCCC1.O1CCOCC1.CO>[N+:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:33][CH2:32][C:31]([O:35][CH3:36])=[O:34])[CH:20]=[C:19]2[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)([O-:15])=[O:14]

Participants

8

Reactant 4

HCID 7294Methyl Acrylate2×HCID 66854Benzyltrimethylammonium hydroxide2×HCID 18926547HCID 18926547, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18926604HCID 18926604, compoundYield 37.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzyltrimethylammonium hydroxide (0.17 ml of 40% solution in methanol) wasadded to a stirred suspension of 5-nitro-3-(3-pyridyl)-1H-indole (0.95 g) and methyl acrylate (0.41 g) in a mixture of tetrahydrofuran (10 ml) and dioxan (15 ml), and the mixture was stirred at room temperature for 2 hours. Methanol (10 ml) was added to give a clear solution followed by further methyl acrylate (0.41 g) and benzyltrimethylammonium hydroxide solution (0.17 ml) and stirring was continued for an additional 18 hours. Potassium t-butoxide (100 mg) was added and stirring was continued for a further 6 hours and the solution was evaporated. The residue was partitioned between ethyl acetate and water and the organic layer was separated and dried (MgSO,). Evaporation of the solvent gave a solid whichwas crystallised from dichloromethane/hexane to give the title compound (0.48 g), m.p. 123°-125° C. Found: C,62.85H,4.62; N,12.91. C17H15N3O4 requires: C,62.76; H,4.65; N,12.92%.

Workup

  1. customto give a clear solution
  2. stirringstirring
  3. waitwas continued for an additional 18 hours
  4. stirringstirring
  5. waitwas continued for a further 6 hours
  6. customthe solution was evaporated
  7. customThe residue was partitioned between ethyl acetate and water
  8. customthe organic layer was separated
  9. dry with materialdried (MgSO,)
  10. customEvaporation of the solvent
  11. customgave a solid whichwas
  12. customcrystallised from dichloromethane/hexane

Sources & evidence

ORD record
ord-7389683bad8a4f20b6f5d45c17e839d1
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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