Triethylamine → HCID 178470056, compound

HRID 2093719Notes

Reaction equation

CCN(CC)CC.[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[C:19](=O)[CH3:20].[CH2:22]([O:24][C:25](=[O:30])[CH2:26][C:27](Cl)=[O:28])[CH3:23].CCOC(C)=O.CCCCCC>C(Cl)Cl.O>[CH2:22]([O:24][C:25]([C:26]1[C:27]([OH:28])=[N:8][C:9]2[C:10]([C:19]=1[CH3:20])=[CH:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)=[O:30])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

12.6 ml (0.09 mol) NEt3 was added to a solution of 16.6 g (0.08 mol) 1-(2-amino-4-(trifluoromethyl)phenyl)ethanone in DCM (170 ml) and cooled to 0° C. 13.4 ml (0.11 mol) 3-chloro-3-oxo-propanoic acid ethyl ester was subsequently added in drops and the mixture was then stirred for 16 h at RT. The mixture was then diluted with water and extracted with DCM (3×). The combined organic phases were dried over Na2SO4 and concentrated in a vacuum. After CC (EtOAc/hexane 2:3) of the residue, 18.1 g (0.07 mol, 87%) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.

Workup

extractionextracted with DCM (3×)
dry with materialThe combined organic phases were dried over Na2SO4
concentrationconcentrated in a vacuum

Sources & evidence

ORD record: ord-8cb1cb5414104e9d8db05bfdb4ed0de6
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445512B2

Reaction notes

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