1,2-Dichlorobenzene → HCID 54724202, compound

HRID 1867058Notes

Reaction equation

HRID 1867058 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[C:4](C)[C:3]=1[CH3:12].[OH:13][C:14]1[CH:19]=[C:18]([CH3:20])[O:17][C:16](=O)[CH:15]=1.Cl[C:23]1C=CC=CC=1Cl>C1(C)C=CC=CC=1>[OH:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:1]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:23])=[O:7])=[CH:4][C:3]=2[CH3:12])[C:16](=[O:17])[CH:15]=1

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 7023624HCID 7023624, compoundHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724202HCID 54724202, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 ml one neck round bottom flask equipped with a stir bar, Dean Stark trap, and condenser 4-amino-2-methyl-methylbenzoate (1.19 g, 11.63 mmol) and 4-hydroxy-6-methyl-2H-pyran-2-one (1.611 g, 12.78 mmol) were mixed together and dissolved in 1,2-dichlorobenzene (5 mL). The mixture was vigorously stirred and then placed in a preheated oil bath at 165 0° C. The reaction was maintained at 165 0° C. for 1.5 hour and cooled to room temperature. The reaction was worked up by diluting with toluene (10 mL) and then stirring at room temperature for 2 hours. A light brown precipitate resulted. The crude product was isolated by filtration and then triturated with ether. 1H NMR (400 MHz, DMSO-d6) δ 10.64 (s, 1H), 7.93 (s, 1H), 7.85 (dd, 8.46 Hz, 1H), 7.26 (d, J=8.12 Hz, 1H), 5.91 (d, J=2.32 Hz, 1H), 5.54 (d, J=2.32 Hz, 1H), 3.84 (s, 3H), 1.99 (s, 3H), 1.73 (s, 3H). ES-HRMS m/z 272.0880 (M−H calcd for C15H14NO4, requires 272.1001).

Workup

  1. customplaced in a preheated oil bath at 165 0° C
  2. temperaturecooled to room temperature
  3. stirringstirring at room temperature for 2 hours
  4. customA light brown precipitate resulted

Sources & evidence

ORD record
ord-f22d59d1b5ad46268043618204564e11
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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