Ethyl 2-methylacetoacetate → HCID 178422302, compound

HRID 1361458Notes

Reaction equation

HRID 1361458 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[C:15]([CH3:16])=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[CH3:17])=[CH:6][CH:5]=1.[CH3:22][CH:23]([C:29]([CH3:31])=O)[C:24](OCC)=[O:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]([F:20])([F:21])[O:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[C:10]([CH3:17])=[C:11]3[C:12](=[CH:14][C:15]=2[CH3:16])[N:13]=[C:29]([CH3:31])[C:23]([CH3:22])=[C:24]3[OH:25])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 6101p-Toluenesulfonic acidHCID 66921796HCID 66921796, compound

Product 1

HCID 178422302HCID 178422302, compoundYield 130.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 1.78 g of 4-(4-trifluoromethoxyphenoxy)-3,5-dimethylaniline, 1.92 g of ethyl 2-methylacetoacetate, and 1.14 g of p-toluenesulfonic acid dissolved in 61 mL of xylene was heated under reflux for 9 hr. This reaction solution was cooled, and the precipitated crystals were then collected by filtration and were washed with distilled water and n-hexane to give 2.94 g of 6-(4-trifluoromethoxyphenoxy)-4-hydroxy-2,3,5,7-tetramethyl-quinoline 2.26 g (yield 100%). A 1.14 g portion in the crystals thus obtained was stirred in 15 mL of acetic anhydride with heating at 120 to 125° C. for 2 hr. The reaction solution was concentrated, ethyl acetate was then added to the concentrate, the mixture was washed with saturated brine, and the solvent was then concentrated under the reduced pressure. The crude product was purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate) to give 0.74 g of 4-acetoxy-6-(4-trifluoromethoxyphenoxy)-2,3,5,7-tetramethyl-quinoline (yield 58.4%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 9 hr
  3. temperatureThis reaction solution was cooled
  4. filtrationthe precipitated crystals were then collected by filtration
  5. washwere washed with distilled water and n-hexane

Sources & evidence

ORD record
ord-047e53cd7b844a1c98814251e1c34afc
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

Loading…