Acetic Acid → HCID 69204021, compound

HRID 2182709Notes

Reaction equation

HRID 2182709 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:15])[N:6]=1)=[O:4].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:34])([CH3:33])[CH2:24][C:25]([OH:32])([C:28]([F:31])([F:30])[F:29])[CH:26]=O)=[C:19]([O:35][CH3:36])[CH:18]=1.C(O)(=O)C.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:15]=[CH:26][C:25]([OH:32])([C:28]([F:29])([F:31])[F:30])[CH2:24][C:23]([C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][C:19]=2[O:35][CH3:36])([CH3:33])[CH3:34])[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 21226206Ethyl acetate hexaneHCID 219489374-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 45089604Methyl 5-aminoquinoline-2-carboxylate

Product 1

HCID 69204021HCID 69204021, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Analogously to Example 1, 250 mg (1.24 mmol) of 5-aminoquinoline-2-carboxylic acid methyl ester is reacted with 484 mg (1.49 mmol) of 4-(4-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 1.40 ml of concentrated acetic acid in 20 ml of toluene. After chromatography on silica gel with hexane-ethyl acetate (0-100%), 500 mg (79% of theory) of the product is obtained.

Sources & evidence

ORD record
ord-2c0a22f2bce44bf6a4969006d9149d79
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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