Acetic Acid → HCID 69204760, compound

HRID 2182712Notes

Reaction equation

HRID 2182712 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:7]=1.[CH3:22][O:23][C:24]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[NH2:36])[N:27]=1)=[O:25].C(O)(=O)C.O>C1(C)C=CC=CC=1.[Ti]>[CH3:22][O:23][C:24]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[N:36]=[CH:11][C:10]([OH:17])([C:13]([F:14])([F:16])[F:15])[CH2:9][C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:20][CH3:21])([CH3:18])[CH3:19])[N:27]=1)=[O:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 21948894HCID 21948894, compoundHCID 45089604Methyl 5-aminoquinoline-2-carboxylate

Product 1

HCID 69204760HCID 69204760, compound

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 1140TolueneSolvent

Procedure

224 mg (0.69 mmol) of 4-(5-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 195 mg (0.96 mmol) of 5-aminoquinoline-2-carboxylic acid methyl ester are dissolved in 20 ml of toluene. After 5.0 ml of concentrated acetic acid is added, it is refluxed for 16 hours in a water separator. After the solvent is removed, the residue is taken up in 10 ml of tetrahydrofuran, 0.3 ml (1.4 mmol) of titanium tetraethylate is added, and the reaction is allowed to reflux again. After the solvent is removed as well as after purification on silica gel with hexane/ethyl acetate (0-100%), 120 mg (33% of theory) of the product is obtained.

Workup

  1. customAfter the solvent is removed
  2. temperatureto reflux again
  3. customAfter the solvent is removed as well as
  4. customafter purification on silica gel with hexane/ethyl acetate (0-100%), 120 mg (33% of theory) of the product
  5. customis obtained

Sources & evidence

ORD record
ord-c10ea811cd63403d8e52467251d16ae4
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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