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

HRID 2173343Notes

Reaction equation

HRID 2173343 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11](Cl)([CH3:13])=[O:12]>C(Cl)Cl>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:12])[CH3:13])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 90496Indan-5-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of indan-5-amine (43 g, 0.31 mol) and TEA (51.3 mL, 0.370 mol) in 400 mL of anhydrous DCM was added a solution of AcCl (23.6 mL, 0.340 mol) in 100 mL of anhydrous DCM dropwise at 0° C. then and stirred for 0.5 h at r.t. After the reaction was completed, the reaction mixture was added 500 mL of DCM, washed with water, 10% HCl solution, 10% NaHCO3 and brine. The organic phase was dried over anhydrous Na2SO4 and concentrated to give N-(2,3-dihydro-1H-inden-5-yl)acetamide. 1H-NMR (300 MHz, CDCl3) δ ppm 7.43 (s, 1H), 7.13˜7.14 (m, 2H), 2.86 (q, J=7.9 Hz, 4H), 2.15 (s, 3H), 2.0˜2.10 (m, 2H);

Workup

  1. washwashed with water, 10% HCl solution, 10% NaHCO3 and brine
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9bba4e81456b42cba3d4a10238e3df51
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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