1,2-Dichlorobenzene → HCID 12593068, compound

HRID 261088Notes

Reaction equation

HRID 261088 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([OH:3])=O.[NH2:14][C:15]([CH3:19])([CH3:18])[CH2:16]O.ClC1C=CC=CC=1Cl>C(OCC)(=O)C>[CH3:16][C:15]1([CH3:19])[N:14]2[C:7](=[O:9])[C:6]3[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=3[CH:4]=[C:1]2[O:3][CH2:18]1

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 118072-Amino-2-methyl-1-propanolHCID 66643Homophthalic acid

Product 1

HCID 12593068HCID 12593068, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1 g. of 2-carboxymethylbenzoic acid, 0.5 g. of 2-amino-2-methylpropanol, and 5 ml. of o-dichlorobenzene was heated to 150°-160° C. for 4 hours. After cooling, the solvent was distilled off from the reaction mixture under reduced pressure and the residue obtained was dissolved in 30 ml. of ethyl acetate. Then, the solution was successively washed with diluted hydrochloric acid, a diluted sodium carbonate solution, and water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. By recrystallizing the residue obtained from cyclohexane, 700 mg. of 3,3-dimethyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-b]isoquinoline was obtained.

Workup

  1. additionA mixture of 1 g
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  4. customthe residue obtained
  5. dissolutionwas dissolved in 30 ml
  6. washThen, the solution was successively washed with diluted hydrochloric acid
  7. dry with materiala diluted sodium carbonate solution, and water, dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customBy recrystallizing the residue
  10. customobtained from cyclohexane, 700 mg

Sources & evidence

ORD record
ord-01c7e97a20e746d9b911478af0345b12
Source dataset
uspto-grants-1979_08
Patent number
US04163844

Reaction notes

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