Oxalic Acid → HCID 20065658, compound

HRID 359121Notes

Reaction equation

HRID 359121 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[CH:24]([OH:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31].[C:35]([OH:40])(=[O:39])[C:36]([OH:38])=[O:37]>CN(C)C=O.C(C(C)=O)C>[C:35]([OH:40])(=[O:39])[C:36]([OH:38])=[O:37].[C:29]([O:26][CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:24](=[O:25])[N:16]1[CH2:15][CH2:14][CH2:13][N:10]1[CH2:9][CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)(=[O:33])[CH:30]([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 24758Sodium hydrideHCID 62325Isobutyryl chlorideHCID 14476373HCID 14476373, compound

Product 1

HCID 20065658HCID 20065658, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

15 A solution of 2-[3-(4-phenyl-1,2,3,6-tetrahydro-1pyridyl)propyl]-3-hydroxy-1-isoindolinone (7 g) in anhydrous dimethylformamide (75 cc) is added to a suspension of sodium hydride (as a 50% suspension in oil) (1 g) in anhydrous dimethylformamide (25 cc) at a temperature close to 20° C. in the course of 10 minutes and agitation is continued for 2 hours. Then, 2.3 g of isobutyryl chloride is added in the course of 5 minutes, and agitation is continued for a further 20 hours. The suspension obtained is poured into distilled water (100 cc) and extracted with methylene chloride (4×50 cc). The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue obtained is dissolved in methyl ethyl ketone (45 cc). A solution of oxalic acid (1.5 g) in methyl ethyl ketone (35 cc) is added and agitation continued for 1 hour at a temperature close to 20° C. The precipitate formed is separated by filtration and recrystallized from boiling methanol (200 cc). 3 g of 3-isobutyryloxy-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone oxalate are thus obtained, melting at 164° C.

Workup

  1. customclose to 20° C. in the course of 10 minutes and agitation
  2. waitis continued for a further 20 hours
  3. customThe suspension obtained
  4. additionis poured
  5. distillationinto distilled water (100 cc)
  6. extractionextracted with methylene chloride (4×50 cc)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  10. customThe residue obtained
  11. waitagitation continued for 1 hour at a temperature
  12. customclose to 20° C
  13. customThe precipitate formed
  14. customis separated by filtration
  15. customrecrystallized

Sources & evidence

ORD record
ord-2a7ae60dec9c4502889ab0a959e9bf69
Source dataset
uspto-grants-1991_03
Patent number
US04999355

Reaction notes

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