2-Methoxyaniline → HCID 178498506, compound

HRID 545197Notes

Reaction equation

HRID 545197 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3]([O:5]C)=O.[CH3:11][O:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].O(C1C=CC=CC=1)C1C=CC=CC=1>CO.C1(C)C=CC=CC=1.CCCCCC>[CH3:10][O:9][C:7]([C:1]1[CH:2]=[C:3]([OH:5])[C:16]2[C:14](=[C:13]([O:12][CH3:11])[CH:19]=[CH:18][CH:17]=2)[N:15]=1)=[O:8]

Participants

7

Reactant 3

HCID 70002-MethoxyanilineHCID 7583Diphenyl EtherHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 178498506HCID 178498506, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

145.6 g of dimethyl acetylenedicarboxylate was dropwise added to a solution of 123.15 g of 2-methoxyaniline in MeOH (600 mL) at 0° C. over 30 minutes. The mixture was stirred at room temperature overnight, and the resulting solution was added to 700 mL of Ph2O heated at 235° C. (inner temperature) over 30 minutes. This was then heated for an additional 30 minutes. After cooled to room temperature, the reaction mixture was diluted with 700 mL of toluene and 700 mL of n-hexane, and stirred at 0° C. for 3 hours. The resulting precipitate was taken out through filtration, washed with MeOH, and 134 g of 4-hydroxy-8-methoxyquinoline-2-carboxylic acid methyl ester was obtained as an off-white solid.

Workup

  1. temperatureheated at 235° C. (inner temperature) over 30 minutes
  2. temperatureThis was then heated for an additional 30 minutes
  3. temperatureAfter cooled to room temperature
  4. stirringstirred at 0° C. for 3 hours
  5. filtrationThe resulting precipitate was taken out through filtration
  6. washwashed with MeOH

Sources & evidence

ORD record
ord-94916087c7e943e19264298344c16447
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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