Methanol → HCID 19696158, compound

HRID 863498Notes

Reaction equation

HRID 863498 reaction equation
[NH2:1][C:2]1[C:3]([N+:16]([O-])=O)=[C:4]2[C:8](=[CH:9][C:10]=1Br)[CH2:7][CH:6]([NH:12][C:13](=[O:15])[CH3:14])[CH2:5]2.[C:19]([O-:22])(=O)[CH3:20].[Na+].C[OH:25]>[Pd]>[O:25]=[C:20]1[NH:16][C:3]2[C:4]3[CH2:5][CH:6]([NH:12][C:13](=[O:15])[CH3:14])[CH2:7][C:8]=3[CH:9]=[CH:10][C:2]=2[NH:1][C:19]1=[O:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 19696253HCID 19696253, compound

Product 1

HCID 19696158HCID 19696158, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of N-(5-amino-6-bromo-4-nitro-indan-2-yl)acetamide (0.5 g, 1.6 mmol), 5% palladium on carbon (0.2 g) and sodium acetate (0.16 g) in methanol (75 mL) was placed on a Parr hydrogenation apparatus under a hydrogen atmosphere (51 psi) and shaken for 18 h. After removing the catalyst by filtration, the solvent was evaporated and the residue was suspended in 2N HCl, treated with oxalic acid (0.5 g) and then heated at 80° C. for 4 h. The water was evaporated and the residue dissolved in saturated sodium bicarbonate and acetic anhydride (1 mL) was added. The resulting solid was collected by filtration and dried in vacuo to give a brown solid (0.15 g) in 36% yield.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. customthe solvent was evaporated
  4. additiontreated with oxalic acid (0.5 g)
  5. customThe water was evaporated
  6. dissolutionthe residue dissolved in saturated sodium bicarbonate
  7. additionacetic anhydride (1 mL) was added
  8. filtrationThe resulting solid was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-cd18a75f1d9b48aba457bd80ae4f19fa
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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