Ethyl 4,4,4-trifluoroacetoacetate → HCID 18416189, compound

HRID 990963Notes

Reaction equation

HRID 990963 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].[F:10][C:11]([F:21])([F:20])[C:12](=O)[CH2:13][C:14](OCC)=[O:15]>C1(C)C=CC=CC=1.OS(O)(=O)=O>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[Cl:9])[NH:6][C:14](=[O:15])[CH:13]=[C:12]2[C:11]([F:21])([F:20])[F:10]

Participants

5

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 888884-Bromo-3-chloroaniline

Product 1

HCID 18416189HCID 18416189, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 1140TolueneSolvent

Procedure

This compound was prepared according to General Method 11 (EXAMPLE 22) from 4-bromo-3-chloroaniline (2.06 g, 10.0 mmol), ethyl 4,4,4-trifluoroacetoacetate (2.30 g, 12.5 mmol) in 50 mL toluene followed by heating in 33 mL conc. H2SO4 to afford 2.08 g (64%) of 6-bromo-7-chloro-4-(trifluoromethyl)-quinolin-2(1H)-one, an off-white solid. This material was converted to the corresponding imino ether according to General Method 12 (EXAMPLE 22) with isopropyl iodide (4.32 g, 25.4 mmol) and CsF (3.85 g, 25.4 mmol) in 32 mL DMF to afford 1.34 g (57%) of 6-bromo-7-chloro-2-isopropoxy-4-(trifluoromethyl)quinoline, a white solid, after flash chromatography (hexanes). Data for 6-bromo-7-chloro-2-isopropoxy-4-(trifluoromethyl)quinoline: 1H NMR (400 MHz, CDCl3) δ 8.22 (broad s, 1H), 8.00 (s, 1H), 7.17 (s, 1H), 5.51 (hept, 1H, J=6.2), 1.40 (d, 6H, J=6.2).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-afc9eed409d14c69aafdc65ecf6c8a81
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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