Acetic Anhydride → N-(5-acetylamino-indan-2-yl)-acetamide

HRID 863492Notes

Reaction equation

HRID 863492 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:14](=[O:16])[CH3:15])[CH2:7]2)([O-])=O.[C:17](OC(=O)C)(=[O:19])[CH3:18].[H][H]>O1CCCC1.[Ni]>[C:17]([NH:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:14](=[O:16])[CH3:15])[CH2:7]2)(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14820512N-(5-nitro-indan-2-yl)-acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 19696254N-(5-acetylamino-indan-2-yl)-acetamideYield 52%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of N-(5-nitro-indan-2-yl)-acetamide (20.5 g, 93 mmol) in tetrahydrofuran (200 mL) was combined with acetic anhydride (10 mL) and Raney nickel (5 g) and stirred under an atmosphere of hydrogen gas (in a balloon) at room temperature for 24 h. Additional Raney nickel was added and the balloon recharged with hydrogen gas and stirred an additional 24 h. After removing the Raney nickel by filtration through a celite pad and washing with methanol several times, the filtrate was evaporated to a syrup. The residue was triturated with ether/water and the resulting white solid collected by filtration (9.2 g, 52% yield overall from 2-aminoindan, prepared in Example 20).

Workup

  1. stirringstirred an additional 24 h
  2. customAfter removing the Raney nickel
  3. filtrationby filtration through a celite pad
  4. washwashing with methanol several times
  5. customthe filtrate was evaporated to a syrup
  6. customThe residue was triturated with ether/water
  7. filtrationthe resulting white solid collected by filtration (9.2 g, 52% yield overall from 2-aminoindan
  8. customprepared in Example 20)

Sources & evidence

ORD record
ord-c15d85db7cec434a938c1f42cc3374b4
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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