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Diethyl Ether → HCID 178470066, compound

HRID 2419825
Notes
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Reaction equation

HRID 2419825 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]([NH:8][C:9]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=O)=[O:7])[CH3:2].CCOCC.CC[O-].[Na+].[Na]>C(O)C>[OH:7][C:6]1[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:23])=[C:11]([OH:13])[C:10]2[C:9](=[C:18]([C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:16][CH:15]=2)[N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 20314294Methyl 2-[(3-ethoxy-1,3-dioxopropyl)amino]-3-(trifluoromethyl)benzoate

Product 1

HCID 178470066HCID 178470066, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

35.66 g of the product of Step B were added to 800 ml of anhydrous ether in the presence of sodium ethylate prepared from 2.69 g of sodium and 54 ml of ethanol and the mixture was vacuum filtered. The recovered precipitate was dissolved in water and the pH of the solution was adjusted to 1 by addition of 20% hydrochloric acid to obtain 30.56 g of ethyl 2,4-dihydroxy-8-trifluoromethyl-quinoline-3-carboxylate melting at 190° C which was used as is for the next step.

Workup

  1. filtrationfiltered
  2. dissolutionThe recovered precipitate was dissolved in water
  3. additionthe pH of the solution was adjusted to 1 by addition of 20% hydrochloric acid

Sources & evidence

ORD record
ord-5e41969ea0c640eab2edfaf63565bb7e
Source dataset
uspto-grants-1978_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04107310

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes