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

HRID 1669006Notes

Reaction equation

HRID 1669006 reaction equation
CC(O[C:5]([CH3:7])=[O:6])=O.[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH2:13][CH2:12]2>O1CCOCC1.O>[CH2:14]1[C:15]2[C:11](=[CH:10][C:9]([NH:8][C:5](=[O:6])[CH3:7])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 90496Indan-5-amine

Product 1

HCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamideYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

Ac2O (44.6 mL, 473 mmol) was added dropwise to a stirred solution of 5-indanamine (1) (30 g, 225 mmol) in dioxane (120 mL) at 0° C. and the solution stirred at 20° C. for 48 h. The solution was diluted with water (500 mL), stirred 20 min and the precipitate filtered. The solid was washed with water (3×30 mL) and air-dried to give acetamide 16 (37.4 g, 95%) as a tan solid: mp 99-101° C.; 1H NMR δ 7.38-7.43 (m, 2H, H-4, NH), 7.10-7.16 (m, 2H, H-6, H-7), 2.85 (br q, J=7.7 Hz, 4H, H-1, H-3), 2.13 (s, 3H, CH3), 2.06 (br, p, J=7.4 Hz, 2H, H-2); 13C NMR δ 168.3, 145.1, 140.3, 136.0, 124.4, 118.2, 116.6, 33.0, 32.3, 25.6, 24.4.

Workup

  1. stirringstirred 20 min
  2. filtrationthe precipitate filtered
  3. washThe solid was washed with water (3×30 mL)
  4. customair-dried

Sources & evidence

ORD record
ord-0b05053b2e904d8e84c004f4ce640e9a
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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