N-(5-nitro-indan-2-yl)-acetamide → N-(5-amino-2,3-dihydro-1H-inden-2-yl)acetamide

HRID 1531272Notes

Reaction equation

HRID 1531272 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(O)C.[Pd]>[NH2:1][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

Participants

4

Reactant 1

HCID 14820512N-(5-nitro-indan-2-yl)-acetamide

Product 1

HCID 14820513N-(5-amino-2,3-dihydro-1H-inden-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(5-nitro-indan-2-yl)-acetamide (Bigge, C. F.; Retz, D. M. WO 9617832 A1) (0.37 g, 1.68 mmol) in ethanol (10 mL) is degassed and 10% palladium on carbon added (0.05 g). The reaction mixture is evacuated and placed under 1 atm H2(g) for 2 h. Fitration of the reaction mixture through Celite is followed by concentration of the filtrate under reduced pressure to give N-(5-amino-indan-2-yl)-acetamide as a white solid which is used directly without further purification. 1H NMR (DMSO-d6, 300 MHz) δ 8.05 (1H, d), 6.82 (1H, d), 6.40 (1H, s), 6.35 (1H, d), 4.81 (2H, bs), 4.38 (1H, m), 2.98 (2H, m), 2.58 (2H, m), 1.81 (3H, s).

Workup

  1. customThe reaction mixture is evacuated

Sources & evidence

ORD record
ord-6344dba2f95f4624bbb1185e0776d93d
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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