Ammonia → HCID 66584742, compound

HRID 1629997Notes

Reaction equation

HRID 1629997 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]([Cl:9])=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=2)[C:6]([C:18]([O:20][CH3:21])=[O:19])=[CH:5]1.Cl.[CH2:23]=O.N>CO.O>[Cl:9][C:8]1[N:4]2[CH2:3][CH2:2][NH:1][CH2:23][C:5]2=[C:6]([C:18]([O:20][CH3:21])=[O:19])[C:7]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 86680812HCID 86680812, compound

Product 1

HCID 66584742HCID 66584742, compoundYield 224.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 8.41 g (27.7 mmol) of methyl 1-(2-amino-ethyl)-5-chloro-4-(3-cyanophenyl)-1H-pyrrole-3-carboxylate in 20 ml of methanol are added 84 ml (340 mmol) of aqueous 4N hydrochloric acid solution. The formation of a white precipitate is rapidly observed and the medium then becomes clear, while the mixture is heated to 90° C. and 0.92 g (10 mmol) of paraformaldehyde is added. Heating is continued at 90° C. for 4 hours. After cooling, the reaction medium is poured into 200 ml of water and the solution is basified by adding aqueous ammonia. The product is extracted with ethyl acetate, the organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give an orange-coloured oil, which is chromatographed on a column of 80 g of silica gel, eluting with a mixture of 2% methanol in dichloromethane, to give 7.1 g of methyl 6-chloro-7-(3-cyanophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylate in the form of a yellow oil.

Workup

  1. temperatureHeating
  2. temperatureAfter cooling
  3. extractionThe product is extracted with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customthe solvent is evaporated off under reduced pressure
  6. customto give an orange-coloured oil, which
  7. customis chromatographed on a column of 80 g of silica gel
  8. washeluting with a mixture of 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-65b8877217314a36b9a555867dbaf330
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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