Oxalic Acid → HCID 21487263, compound

HRID 1414383Notes

Reaction equation

HRID 1414383 reaction equation
Cl[CH2:2][CH:3]([CH3:22])[CH2:4][O:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[CH:29]([NH2:32])([CH3:31])[CH3:30]>CC(C)=O>[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[CH:29]([NH:32][CH2:2][CH:3]([CH3:22])[CH2:4][O:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 6363IsopropylamineHCID 21487255HCID 21487255, compound

Product 1

HCID 21487263HCID 21487263, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
2 °C

Procedure

A solution of 3-(3-chloro-2-methylpropoxy)-2-phenyl-isoindolin-1-one (24.7 g.) in isopropylamine (250 cc.) is heated in an autoclave at 120°C. for 24 hours. After cooling, the reaction mixture is concentrated to dryness under reduced pressure and the residue is then taken up in a 5N aqueous solution of sodium hydroxide (30 cc.), water (200 cc.) and diethyl ether (200 cc.). The ether solution is washed three times with distilled water (total 150 cc.) and is extracted four times with a 2N aqueous solution of methanesulphonic acid (total 200 cc.). The acid solution is washed three times with diethyl ether (total 150 cc.) and is then rendered alkaline by adding 10N sodium hydroxide solution (50 cc.). The oil which separates out is extracted four times with diethyl ether (total 200 cc.). The organic extracts are combined, washed five times with distilled water (total 250 cc.), dried over anhydrous magnesium sulphate and concentrated to dryness under reduced pressure. The residue obtained (22.2 g.) is dissolved in acetone (130 cc.). A solution of oxalic acid (6.2 g.) in acetone (30 cc.) is added to the solution obtained. After cooling for 3 hours at 2°C., the product which has crystallised is filtered off and washed twice with acetone (total 20 cc.) and then with diethyl ether (30 cc.). After drying, 3-(3-isopropylamino-2-methylpropoxy)-2-phenyl-isoindolin-1-one hydrogen oxalate (26.6 g.), which melts at 150°C., is obtained.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  3. washThe ether solution is washed three times with distilled water (total 150 cc.)
  4. extractionis extracted four times with a 2N aqueous solution of methanesulphonic acid (total 200 cc.)
  5. washThe acid solution is washed three times with diethyl ether (total 150 cc.)
  6. additionby adding 10N sodium hydroxide solution (50 cc.)
  7. extractionThe oil which separates out is extracted four times with diethyl ether (total 200 cc.)
  8. washwashed five times with distilled water (total 250 cc.)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe residue obtained (22.2 g.)
  12. customobtained
  13. customthe product which has crystallised
  14. filtrationis filtered off
  15. washwashed twice with acetone (total 20 cc.)
  16. customAfter drying

Sources & evidence

ORD record
ord-29f9b143dbb34e78a4edbdb8bfb7717b
Source dataset
uspto-grants-1977_01
Patent number
US04001271

Reaction notes

Loading…