HCID 13189130, compound → HCID 20488298, compound

HRID 1995325Notes

Reaction equation

HRID 1995325 reaction equation
NC1C2=C3N(C(C)CC2)C=C(C(O)=O)C(=O)C3=CC=1.[CH3:20][CH:21]1[N:30]2[C:25]3[C:26](=[CH:35][CH:36]=[C:37]([N:38]4[CH:42]=[CH:41][CH:40]=[CH:39]4)[C:24]=3[CH2:23][CH2:22]1)[C:27](=[O:34])[C:28]([C:31]([OH:33])=[O:32])=[CH:29]2.[H][H]>FC(F)(F)C(O)=O.[Rh]>[CH3:20][CH:21]1[N:30]2[C:25]3[C:26](=[CH:35][CH:36]=[C:37]([N:38]4[CH2:42][CH2:41][CH2:40][CH2:39]4)[C:24]=3[CH2:23][CH2:22]1)[C:27](=[O:34])[C:28]([C:31]([OH:33])=[O:32])=[CH:29]2

Participants

6

Reactant 3

HCID 13189130HCID 13189130, compoundHCID 70530913HCID 70530913, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20488298HCID 20488298, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Using the method of Example 5, 3.0 g of 8-amino-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid was converted to 6,7-dihydro-5-methyl-1-oxo-8-(1-pyrryl)-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. The crude product was dissolved in 50 ml of trifluoroacetic acid and 2 g of rhodium on alumina was added. The mixture was hydrogenated at 20° C. for 18 hours at 50 psi of hydrogen gas. The mixture was filtered, evaporated to dryness and dissolved in 10 percent sodium hydroxide solution. The solution was acidified with glacial acetic acid. The product was recrystallized from N,N-dimethyformamide to provide tan crystals of 6,7-dihydro-5-methyl-1-oxo-8-(1-pyrrolidyl)-1H,5H-benzo[ij]quinolizine-2-carboxylicacid, m.p. 170°-174° C. Nuclear magnetic resonance analysis showed water and N,N-dimethyl formamide present in the solid. Analysis: Calculated for C18H20N2O3.1/10(CH3)2NCHO.1/2H2O: %C, 66.8; %H, 6.6; %N, 9.2; Found: %C, 66.7; %H, 6.2; %N, 9.2.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness
  3. dissolutiondissolved in 10 percent sodium hydroxide solution
  4. customThe product was recrystallized from N,N-dimethyformamide

Sources & evidence

ORD record
ord-b5be45d77895419f8b2422324f1c909e
Source dataset
uspto-grants-1983_09
Patent number
US04404207

Reaction notes

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