Methanol → HCID 19696277, compound

HRID 863527Notes

Reaction equation

HRID 863527 reaction equation
N#N.Cl.C[CH:5]1[C:13]2[C:8](=[C:9]([N+:16]([O-])=O)[C:10]([NH2:15])=[C:11](Br)[CH:12]=2)[CH2:7][CH:6]1[NH2:19].[C:20]([OH:25])(=O)[C:21](O)=[O:22].[CH3:26]O>[Pd]>[CH3:26][NH:19][CH:6]1[CH2:7][C:8]2[C:9]3[NH:16][C:20](=[O:25])[C:21](=[O:22])[NH:15][C:10]=3[CH:11]=[CH:12][C:13]=2[CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 971Oxalic AcidHCID 86752147HCID 86752147, compound

Product 1

HCID 19696277HCID 19696277, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of N2 -methyl-2,5-diamino-6-bromo-4-nitroindane hydrochloride (17.2 g, 53 mmol) and 20% Pd/C (1 g) in methanol (250 mL) was shaken on a Parr hydrogenation apparatus under a hydrogen atmosphere (50 psi) for 6 h. After removing the catalyst, the filtrate was evaporated and the residue taken up in 2N HCl 250 mL) and oxalic acid (13 g, 0.1 mmol) and heated at 100° C. for 5 h. The mixture was cooled in a refrigerator overnight, and the resulting precipitate was collected by filtration and washed with water and then diethyl ether and dried to give the product (9.9 g).

Workup

  1. customAfter removing the catalyst
  2. customthe filtrate was evaporated
  3. temperatureThe mixture was cooled in a refrigerator overnight
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water
  6. dry with materialdiethyl ether and dried

Sources & evidence

ORD record
ord-8bdb4c0f7afc4e8b96448196d253a50c
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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