HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → Ethyl 4-ethyl-7-fluoro-6-methoxy-2-oxo-1,2-dihydro-3-quinolinecarboxylate

HRID 1007867
Notes
Print preview

Reaction equation

HRID 1007867 reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[NH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([O:18][CH3:19])=[CH:13][C:12]=1[C:20](=O)[CH2:21][CH3:22].C(N([CH2:29][CH3:30])CC)C.CC[O-:33].[Na+]>C(#N)C.O>[CH2:21]([C:20]1[C:12]2[C:11](=[CH:16][C:15]([F:17])=[C:14]([O:18][CH3:19])[CH:13]=2)[NH:10][C:7](=[O:8])[C:3]=1[C:4]([O:5][CH2:29][CH3:30])=[O:33])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2723922Sodium ethoxideHCID 10104164HCID 10104164, compoundHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 21892008Ethyl 4-ethyl-7-fluoro-6-methoxy-2-oxo-1,2-dihydro-3-quinolinecarboxylateYield 85.3%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent2×

Procedure

A solution of ethylmalonyl chloride (12.9 ml, 100 mmol) in anhydrous acetonitrile (30 ml) is added dropwise, under argon and at 0° C. to a solution of 1-(2-amino-4-fluoro-5-methoxyphenyl)-1-propanone (15.3 g, 77.5 mmol) and triethylamine (13.9 ml, 100 mmol) in anhydrous acetonitrile (110 ml). The reaction medium is left to return to ambient temperature, a solution of sodium ethylate (obtained by 1.8 g, 78 mmol of sodium in 80 ml of ethanol) is cannulated dropwise and under argon, then the reaction medium is left under agitation for 12 hours at ambient temperature. The reaction mixture is poured into ice-cooled water (100 ml) and agitation is carried out for two hours, then the precipitate is filtered out and washed with water, with ethanol and with ether. 19.4 g of a white solid is obtained.

Workup

  1. waitThe reaction medium is left
  2. customto return to ambient temperature
  3. additionThe reaction mixture is poured into ice-
  4. waitis carried out for two hours
  5. filtrationthe precipitate is filtered out
  6. washwashed with water, with ethanol and with ether

Sources & evidence

ORD record
ord-62d32b041ea1483e999e6e9f76797894
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06797715B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes