3-Methylpyridine → HCID 13586193, compound

HRID 868035Notes

Reaction equation

HRID 868035 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].N1C=CC=C(C)C=1.[CH2:26]([NH:28][CH2:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)[CH3:27]>[OH-].[NH4+]>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:32]3[CH2:33][CH2:34][CH:30]([CH2:29][NH:28][CH2:26][CH3:27])[CH2:31]3)[CH:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]

Participants

5

Reactant 3

HCID 79703-MethylpyridineHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 13586193HCID 13586193, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of 2.70 g (10.0 mmole) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 60 ml of β-picoline and 3.85 g (30.0 mmole) of N-ethyl-3-pyrrolidinemethanamine were refluxed overnight. Reaction mixture was cooled to room temperature, 100 ml concentrated ammonium hydroxide added, and the solvents removed at reduced pressure. A solution of 200 ml dichloromethane/ether (1:3) was added. The resulting precipitate was filtered, washed with ethanol/ether (1:3) and finally with ether until dry to give 1.87 g of 1-ethyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 248°-252° C.

Workup

  1. temperaturewere refluxed overnight
  2. customReaction mixture
  3. customthe solvents removed at reduced pressure
  4. additionA solution of 200 ml dichloromethane/ether (1:3) was added
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with ethanol/ether (1:3) and finally with ether
  7. customuntil dry

Sources & evidence

ORD record
ord-3cdf07d7f7a242afaf4fff4a54690f8f
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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