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Acetic Acid → 2-Methyl-7-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester

HRID 841772
Notes
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Reaction equation

HRID 841772 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([C:13]2[C:14]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:5]=[CH:6][C:7]=1C=O.[C:29]([O:35][CH2:36][CH3:37])(=[O:34])[CH2:30][C:31]([CH3:33])=O.[OH-].[Na+].[C:40](O)(=O)C>O>[CH2:36]([O:35][C:29]([C:30]1[C:31]([CH3:33])=[N:1][C:2]2[C:7]([CH:40]=1)=[CH:6][CH:5]=[C:4]([NH:10][C:11]([C:13]1[C:14]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:23][CH:24]=3)=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:12])[CH:3]=2)=[O:34])[CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 14798Sodium HydroxideHCID 101346044'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-amino-4-formyl-phenyl)-amide

Product 1

HCID 698903792-Methyl-7-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4′-Trifluoromethyl-biphenyl-2-carboxylic acid (3-amino-4-formyl-phenyl)-amide (769 mg, 2.0 mmol) and ethyl acetoacetate (260 mg, 2.0 mmol) were dissolved in 10 ml of acetic acid and heated at 80 C. After 2.5 h, the mixture was cooled to room temperature, diluted with water and brought to pH 10 with 2N NaOH. The mixture was extracted with ethyl acetate (2×50 ml), the combined organic layers washed with brine, dried over magnesium sulfate, and concentrated to give 815 mg of a yellow solid. This material was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in dichloromethane to provide 349 mg (36%) of the title compound as a yellow foam.

Workup

  1. temperatureheated at 80 C
  2. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-732dea66da874e72a06cb8339b87576d
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06369075B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes