Pyridine → N-(2,3-Dihydro-1H-inden-5-yl)acetamide

HRID 1289216Notes

Reaction equation

HRID 1289216 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[C:11](OC(=O)C)(=[O:13])[CH3:12].N1C=CC=CC=1>C(OCC)(=O)C>[C:11]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 90496Indan-5-amine

Product 1

HCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-aminoindan (100 g), acetic anhydride (84 g), pyridine (65 g) and ethyl acetate (500 ml) was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was triturated under diethyl ether (800 ml). The solid was filtered off, washed with diethyl ether (500 ml) and with hexane (500 ml) and dried. There was thus obtained 5-acetamidoindan (104.5 g), m.p. 107° C.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated under diethyl ether (800 ml)
  3. filtrationThe solid was filtered off
  4. washwashed with diethyl ether (500 ml) and with hexane (500 ml)
  5. customdried

Sources & evidence

ORD record
ord-57e0b842f60e47fa848b3663aebd5b19
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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