Stannous chloride dihydrate → 4-Methyl-2-propyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

HRID 2093712Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12](=O)[CH3:13].[CH2:15]([O:17][C:18](=[O:25])[CH2:19][C:20](=O)[CH2:21][CH2:22][CH3:23])[CH3:16].O.O.[Sn](Cl)Cl.C(Cl)Cl.CCCCCC>CCO>[CH2:15]([O:17][C:18]([C:19]1[C:20]([CH2:21][CH2:22][CH3:23])=[N:1][C:2]2[C:3]([C:12]=1[CH3:13])=[CH:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=2)=[O:25])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

5.0 g (24.6 mmol) 1-(2-amino-4-(trifluoromethyl)phenyl)ethanone was stirred together with 2.6 ml (24.6 mmol) 3-oxo-hexanoic acid ethyl ester and 5.6 g (24.6 mmol) tin(II) chloride dihydrate for 3 h at RT. The mixture was subsequently heated to 80° C. for 16 h. After cooling to RT, the mixture was diluted with EtOH (25 ml), ice was added and the mixture was stirred for 10 min at RT. The solution was subsequently filtered off and washed with EtOAc. The phases were separated and the aqueous phase was extracted with EtOAc. The organic phases were combined, washed with an aq. Na2-EDTA sol., water and brine, dried over MgSO4 and concentrated in a vacuum. After CC (DCM/hexane 2:1) of the residue, 4.3 g (13.7 mmol, 56%) 4-methyl-2-propyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.

Workup

temperatureAfter cooling to RT
additionwas added
filtrationThe solution was subsequently filtered off
washwashed with EtOAc
customThe phases were separated
extractionthe aqueous phase was extracted with EtOAc
washwashed with an aq. Na2-EDTA sol., water and brine
dry with materialdried over MgSO4
concentrationconcentrated in a vacuum

Sources & evidence

ORD record: ord-bc0008c82b4f488984ab972966294aa8
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445512B2

Reaction notes

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