Ethyl 2-methylacetoacetate → HCID 178492457, compound

HRID 1361456Notes

Reaction equation

HRID 1361456 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[NH2:5].[CH3:18][CH:19]([C:25]([CH3:27])=O)[C:20](OCC)=[O:21].ClC1C(OC2C=CC(OC)=CC=2)=CC=C2C=1C(O)=C(C)C(C)=N2>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:6]([C:20]([OH:21])=[C:19]([CH3:18])[C:25]([CH3:27])=[N:5]2)=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 12806998HCID 12806998, compoundHCID 178492460HCID 178492460, compound

Product 1

HCID 178492457HCID 178492457, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture composed of 2.9 g of 3-chloro-4-(4-methoxyphenoxy)-aniline, 2.9 g of ethyl 2-methylacetoacetate, and 0.5 mL of ethanol was added dropwise to 4.2 g of polyphosphoric acid heated to 150° C. This reaction solution was stirred at 140 to 150° C. while removing ethanol by evaporation for 3 hr and was then poured into 195 mL of iced water containing 2 mL of concentrated hydrochloric acid. The crystals were collected by filtration and were washed with n-hexane to give 3.29 g of a mixture of 5-chloro-6-(4-methoxyphenoxy)-4-hydroxy-2,3-dimethyl-quinoline with 7-chloro-6-(4-methoxyphenoxy)-4-hydroxy-2,3-dimethyl-quinoline (yield 100%).

Workup

  1. customwhile removing ethanol
  2. customby evaporation for 3 hr
  3. additionwas then poured into 195 mL of iced water containing 2 mL of concentrated hydrochloric acid
  4. filtrationThe crystals were collected by filtration
  5. washwere washed with n-hexane

Sources & evidence

ORD record
ord-f0b1b7cf7fb84aa799d2fafadf11e14e
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

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