Oxalic Acid → HCID 19696145, compound

HRID 863519Notes

Reaction equation

HRID 863519 reaction equation
[NH2:1][C:2]1[C:3]([N+:15]([O-])=O)=[C:4]2[C:8](=[CH:9][C:10]=1Br)[CH2:7][CH:6]([C:12]([OH:14])=[O:13])[CH2:5]2.[C:18](O)(=[O:22])[C:19](O)=[O:20]>C(O)C.O1CCCC1.Cl.[Pd]>[O:20]=[C:19]1[NH:15][C:3]2[C:4]3[CH2:5][CH:6]([C:12]([OH:14])=[O:13])[CH2:7][C:8]=3[CH:9]=[CH:10][C:2]=2[NH:1][C:18]1=[O:22]

Participants

7

Reactant 2

HCID 971Oxalic AcidHCID 19696199HCID 19696199, compound

Product 1

HCID 19696145HCID 19696145, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-amino-6-bromo-4-nitroindane-2-carboxylic acid (5.5 g, 18 mmol) and 20% Pd/C (0.5 g) in 95% ethanol (250 mL) and tetrahydrofuran (250 mL) was shaken on a Parr hydrogenation apparatus under a hydrogen atmosphere (51 psi) for 30 h. After removing the catalyst, the solvent was evaporated to give a solid. The solid was dissolved in 2N HCl (150 mL) and treated with oxalic acid (4.6 g), and then the mixture was heated at 90° C. for 5 h. After cooling to room temperature, the precipitate was collected by filtration and dried in vacuo (4.0 g).

Workup

  1. customAfter removing the catalyst
  2. customthe solvent was evaporated
  3. customto give a solid
  4. temperatureAfter cooling to room temperature
  5. filtrationthe precipitate was collected by filtration
  6. customdried in vacuo (4.0 g)

Sources & evidence

ORD record
ord-f5006b6bc5064bffbd7353d0879ba07d
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

Loading…