Hydrochloric Acid → 3,3-dimethyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-b]isoquinoline

HRID 1156300Notes

Reaction equation

HRID 1156300 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.Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72391,2-DichlorobenzeneHCID 118072-Amino-2-methyl-1-propanolHCID 66643Homophthalic acid

Product 1

HCID 125930683,3-dimethyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-b]isoquinoline

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 wased 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. dry with materiala diluted sodium carbonate solution, and water, dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customBy recrystallizing the residue
  9. customobtained from cyclohexane, 700 mg

Sources & evidence

ORD record
ord-ab048e8d76c84ad2bbe21175ac32b932
Source dataset
uspto-grants-1982_06
Patent number
US04335129

Reaction notes

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