N-methyl-2-pyrrolidone → HCID 68463346, compound

HRID 269775Notes

Reaction equation

HRID 269775 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:14])=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH3:18][N:19]1[CH2:23][CH2:22][CH2:21][C:20]1=O.C(=O)(O)[O-].[Na+]>CCOCC>[N+:15]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:9]1[CH2:10][CH2:5][CH:18]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:7][CH2:8]1)[NH:9][CH:8]=[C:7]([C:12]#[N:13])[C:6]2=[O:14])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 178510305HCID 178510305, compound

Product 1

HCID 68463346HCID 68463346, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.3 g (5.21 mmol) of 7-chloro-4-hydroxy-6-nitro-3-quinolinecarbonitrile (U.S. Pat. No. 6,297,258) and 2.6 g (16.67 mmol) of 4-(1-pyrrolidine)piperidine 17.0 ml of 1-methyl 2-pyrrolidinone is heated at 120° C. for 5 hours. The mixture is cooled to room temperature and stirred with 15 mL of saturated solution of sodium bicarbonate. Following removal of solvents in vacuo, a residue is obtained, which is stirred with ether. The solid is collected by filtration and washed with ether. The crude product is dissolved in 9:1 methylene chloride/methanol, filtered through a pad of Celite (to remove inorganic material) and further washed with 9:1 methylene chloride/methanol. Evaporation of the filtrate to dryness yields a glassy residue. Purification by silica gel chromatography (gradient 9:1 methylene chloride/methanol to 4:1 methylene chloride/methanol) gives 1.3 g of 6-nitro-4-oxo-7-(4-pyrrolidin-1-ylpiperidin-1-yl)-1,4-dihydroquinoline-3-carbonitrile as an orange solid, mp 232-235° C.

Workup

  1. customremoval of solvents in vacuo
  2. customa residue is obtained
  3. filtrationThe solid is collected by filtration
  4. washwashed with ether
  5. dissolutionThe crude product is dissolved in 9:1 methylene chloride/methanol
  6. filtrationfiltered through a pad of Celite (to remove inorganic material)
  7. washfurther washed with 9:1 methylene chloride/methanol
  8. customEvaporation of the filtrate to dryness
  9. customyields a glassy residue
  10. customPurification by silica gel chromatography (gradient 9:1 methylene chloride/methanol to 4:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-918b3784eb8c4908a2f3fc5b01b98c5f
Source dataset
uspto-grants-2008_11
Patent number
US07449460B2

Reaction notes

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