Pyrrolidine → HCID 54680203, compound

HRID 414733Notes

Reaction equation

HRID 414733 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.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C=O)C.C(Cl)Cl>[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[NH+:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 54706820HCID 54706820, compound

Product 1

HCID 54680203HCID 54680203, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-bromo-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one (2 g) in a mixture of pyrrolidine (10 mL) and DMF (5 mL) was stirred and heated at 100° C. for 2 days. The resulting mixture was then cooled, diluted with CH2Cl2 (100 mL) and filtered. The solid was triturated with hot CHCl3, filtered, and dried to yield the desired product, m.p. 282°-284° C.

Workup

  1. temperatureThe resulting mixture was then cooled
  2. filtrationfiltered
  3. customThe solid was triturated with hot CHCl3
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-99cdcbec318e40ee83f1820ed418b914
Source dataset
uspto-grants-1988_12
Patent number
US04794116

Reaction notes

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