Water → HCID 67725462, compound

HRID 1591156Notes

Reaction equation

HRID 1591156 reaction equation
Cl.[N+:2]([C:5]1[CH:18]=[C:17]2[C:8]([CH2:9][C:10]3([C:16]2=[O:19])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=[CH2:21].C([O-])(=O)C.[Na+].O>CO>[N+:2]([C:5]1[CH:18]=[C:17]2[C:8]([CH2:9][C:10]3([C:16]2=[O:19])[CH2:15][CH2:14][N:13]([CH2:21][CH2:20][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:12][CH2:11]3)=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 75212-VinylpyridineHCID 517045Sodium AcetateHCID 19045345HCID 19045345, compound

Product 1

HCID 67725462HCID 67725462, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.150 g (0.53 mmole) 1,3-dihydro-6-nitro-1-oxospiro[2H-indene-2,4'-piperidine] hydrochloride, 0.116 g (1.1 mmoles) 2-vinylpyridine, and 0.090 g (1.1 mmoles) sodium acetate in 1.5 ml of 1:1 methanol: water was heated at reflux for 8 hours. Ethanol was removed in vacuo. The aqueous residue was diluted with 3 ml saturated sodium bicarbonate solution and extracted with 2×10 ml ethyl acetate. The combined extracts were washed with 3 ml water brine, dried, and the solvent was removed in vacuo to give 0.195 g crude product. This was recrystallized from ethyl acetate to give 0.123 g (66%) product, m.p. 142°-144° C.

Workup

  1. temperatureat reflux for 8 hours
  2. customEthanol was removed in vacuo
  3. additionThe aqueous residue was diluted with 3 ml saturated sodium bicarbonate solution
  4. extractionextracted with 2×10 ml ethyl acetate
  5. washThe combined extracts were washed with 3 ml water brine
  6. customdried
  7. customthe solvent was removed in vacuo
  8. customto give 0.195 g crude product
  9. customThis was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-18a4934b865449449717f2ab3c3af064
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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