Oxalic Acid → HCID 12812488, compound

HRID 1701828Notes

Reaction equation

HRID 1701828 reaction equation
C(O)(=O)/C=C\C(O)=O.[CH3:9][CH:10]([N:17]1[CH2:20][CH:19]([OH:21])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+].[Cl:24][C:25]1[CH:26]=[C:27](F)[CH:28]=[CH:29][CH:30]=1.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>[OH-].[K+].C1C=CC=CC=1.CN(C)C=O>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[Cl:24][C:25]1[CH:30]=[C:29]([CH:28]=[CH:27][CH:26]=1)[O:21][CH:19]1[CH2:20][N:17]([CH:10]([CH3:9])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:18]1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 24758Sodium hydrideHCID 2230871-Chloro-3-fluorobenzeneHCID 12812484HCID 12812484, compound

Product 1

HCID 12812488HCID 12812488, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 67594516HCID 67594516, compoundSolvent

Conditions

Temperature
90 °C

Procedure

1-(α-Methylbenzyl)-3-hydroxyazetidine maleate (393 g., 1.3 moles) was partitioned in dilute potassium hydroxide-benzene. The separated dried benzene solution was concentrated, the residual oil dissolved in 250 ml. of dimethylformamide and added dropwise to a stirred suspension of 53 g. (1.1 moles) of 50% sodium hydride in 750 ml. of dimethylformamide at 90° C. The mixture was heated at 90° C. for 1 hr. and 130.5 g. (1 mole) of 3-chlorofluorobenzene added dropwise at 90° C. The mixture was refluxed for 3 hrs., cooled and partitioned between isopropyl ether and dilute sodium hydroxide. The isopropyl ether solution was dried, concentrated, and the residue added to 1200 ml. of isopropyl alcohol containing 90 g. (1 mole) of oxalic acid. The oxalate salt was recrystallized from ethanol. Yield 263 g. (69%); m.p. 141°-144° C.

Workup

  1. concentrationThe separated dried benzene solution was concentrated
  2. dissolutionthe residual oil dissolved in 250 ml
  3. additionof dimethylformamide and added dropwise to a stirred suspension of 53 g
  4. customat 90° C
  5. temperatureThe mixture was refluxed for 3 hrs
  6. temperature, cooled
  7. custompartitioned between isopropyl ether and dilute sodium hydroxide
  8. dry with materialThe isopropyl ether solution was dried
  9. concentrationconcentrated
  10. additionthe residue added to 1200 ml
  11. customThe oxalate salt was recrystallized from ethanol

Sources & evidence

ORD record
ord-f949f2649f67458198995007116ee1db
Source dataset
uspto-grants-1983_04
Patent number
US04379151

Reaction notes

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