Water → HCID 178423901, compound

HRID 1829159Notes

Reaction equation

HRID 1829159 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[F:9][C:10]([F:20])([F:19])[C:11](=O)[CH2:12][C:13](OCC)=[O:14].O>P(=O)(O)(O)O>[F:9][C:10]([F:20])([F:19])[C:11]1[CH:12]=[C:13]([OH:14])[C:5]2[C:3](=[C:2]([CH3:1])[CH:8]=[CH:7][CH:6]=2)[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7242O-ToluidineHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 178423901HCID 178423901, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
105 °C

Procedure

2-Methylaniline (5.00 g) was dissolved in 75% phosphoric acid (20 mL), and ethyl trifluoroacetoacetate (8.60 g) was dropwise added thereto at 105° C. The mixture was stirred at 105° C. for 5.5 hr. After allowing to cool, the reaction mixture was added to water. The precipitated solid was collected by filtration to give 2-trifluoromethyl-4-hydroxy-8-methylquinoline (1.84 g).

Workup

  1. customat 105° C
  2. temperatureto cool
  3. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-8145cb04aa234de6a4b87cef085dc5ea
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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