Ammonia → HCID 54240079, compound

HRID 1974258Notes

Reaction equation

HRID 1974258 reaction equation
[CH2:1]1[C:13]2[C:4](=[N:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH:12]=2)[CH:3]([C:14]([O:16]C)=O)[CH2:2]1.[NH3:18]>CO>[CH2:1]1[C:13]2[C:4](=[N:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH:12]=2)[CH:3]([C:14]([NH2:18])=[O:16])[CH2:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21489229Methyl 2,3-dihydro-1H-cyclopenta[b]quinoline-3-carboxylate

Product 1

HCID 54240079HCID 54240079, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,3-Dihydro-1H-cyclopenta[b] quinoline in ether is added to isopropylmagnesium bromide (prepared from magnesium and isopropylbromide in ether). The mixture is heated at 120° C for several hours adding toluene when necessary as the ether distilled off to maintain the contents liquid. The mixture is cooled and ether is added. The resulting solution of 2,3-dihydro-1H-cyclopenta[b]-quinoline-3-magnesium bromide is added to stirred ice-cooled ether while a stream of dry CO2 gas is bubbled through until the red colour is discharged. The resulting solid (the magnesium bromide salt of 2,3-dihydro-1H-cyclopenta[b] quinoline-3-carboxylic acid) is dried and added to methanol saturated with HCl. The solution is stirred overnight and then evaporated to dryness. The residue is dissolved in water and extracted with ether. The aqueous phase is basified with sodium carbonate, any solid filtered off and the aqueous solution is extracted with ether (3 times). The ether extracts are dried and evaporated to dryness leaving an oil which is purified by distillation under reduced pressure to give methyl 2,3-dihydro-1H-cyclopenta[b] quinoline-3-carboxylate. This ester is dissolved in methanol saturated with ammonia in a bomb and kept overnight at 80° C. The solution is then cooled and evaporated to dryness. Purification and recrystallisation of the product gives 2,3-dihydro-1H-cyclopenta [b] quinoline-3-carboxamide.

Workup

  1. temperatureThe solution is then cooled
  2. customevaporated to dryness
  3. customPurification and recrystallisation of the product

Sources & evidence

ORD record
ord-16c36adbdd2d4126acc993904cc69b35
Source dataset
uspto-grants-1976_12
Patent number
US04000278

Reaction notes

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