1-Methylpyrrolidine → HCID 54706829, compound

HRID 414732Notes

Reaction equation

HRID 414732 reaction equation
Br[C:2]1[C:3](=[O:19])[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[C:10]([C:11]=1[OH:12])=[CH:9][CH:8]=[CH:7][N:6]=2.[CH3:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[OH-:12].[OH:12][C:11]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3](=[O:19])[C:2]=1[N+:21]1([CH3:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 84541-MethylpyrrolidineHCID 54706820HCID 54706820, compound

Product 1

HCID 54706829HCID 54706829, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In dry pyridine (30 mL), 3-bromo-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one (10 g) was suspended. N-methyl pyrrolidine (20 mL) was added to the suspension. The mixture was heated to 95°-100° C. with stirring, and was kept there for about 33 hours. The product was evaporated under high vacuum to provide a dark oil. This oil was slurried with 200 mL of CH3CN(40): H2O(60): CH3CO2H(1) and filtered. The solid residue on the filter was rinsed with water and the filtrate was evaporated to remove most of the CH3CN. Reversed phase chromatography through an E. Merck RP-8 LoBar column, eluting with increasing concentrations of CH3CN in H2O (containing 1% CH3CO2H) gave a moderately pure product which was subjected to a second chromatographic separation using the same conditions as above. Fractions containing the product were combined and evaporated to yield a solid which was recrystallized from CH2Cl2 /isopropanol to yield the desired product, m.p. 245°-250° C.

Workup

  1. temperatureThe mixture was heated to 95°-100° C.
  2. customThe product was evaporated under high vacuum
  3. customto provide a dark oil
  4. filtrationH2O(60): CH3CO2H(1) and filtered
  5. washThe solid residue on the filter was rinsed with water
  6. customthe filtrate was evaporated
  7. customto remove most of the CH3CN
  8. washMerck RP-8 LoBar column, eluting
  9. temperaturewith increasing concentrations of CH3CN in H2O (containing 1% CH3CO2H)
  10. customgave a moderately pure product which
  11. customwas subjected to a second chromatographic separation
  12. additionFractions containing the product
  13. customevaporated
  14. customto yield a solid which
  15. customwas recrystallized from CH2Cl2 /isopropanol

Sources & evidence

ORD record
ord-ffbe072a9cf14890885546727d1ac0c2
Source dataset
uspto-grants-1988_12
Patent number
US04794116

Reaction notes

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