Ammonia → HCID 13654876, compound

HRID 1199401Notes

Reaction equation

HRID 1199401 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH:7]=[CH:8][C:9](=O)[CH2:10]C(OCC)=O)([O-:3])=[O:2].O=[C:21]([CH2:28][O:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[NH3:36]>C(O)C>[CH2:26]([O:25][C:23]([C:8]1[CH:7]([C:6]2[CH:17]=[CH:18][CH:19]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:21]([CH2:28][O:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[NH:36][C:9]=1[CH2:10][O:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21253101Ethyl 3-oxo-4-[(pyridin-3-yl)oxy]butanoateHCID 53828414HCID 53828414, compound

Product 1

HCID 13654876HCID 13654876, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-nitrobenzylideneacetoacetate (6.47 g. 0.026 mol), ethyl 3-oxo-4-(3-pyridyloxy)butanoate (5.8 g, 0.026 mol) and 0.88 ammonia (2.5 ml) in ethanol were refluxed for 7 hours. The solvent was removed under reduced pressure and the residue partitioned between 2N hydrochloric acid and diethyl ether. The aqueous acid was extracted with chloroform and this was washed with dilute ammonia solution, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica with first chloroform then ethyl acetate as eluent to obtain the title compound. This was dissolved in ethanol and acidified with ethanolic HCl to give the dihydrochloride salt of the title compound (0.95 g) m.p. 206-208° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between 2N hydrochloric acid and diethyl ether
  3. extractionThe aqueous acid was extracted with chloroform
  4. washthis was washed with dilute ammonia solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by chromatography on silica with first chloroform

Sources & evidence

ORD record
ord-2a6a250c2c2646d4ac6f09cad2a0853c
Source dataset
uspto-grants-1990_02
Patent number
US04900750

Reaction notes

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