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

HRID 2104256Notes

Reaction equation

HRID 2104256 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C([O-])([O-])=O.[Na+].[Na+].[C:17](Cl)(=[O:19])[CH3:18]>C(OCC)(=O)C.O>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH:2]1[NH:1][C:17](=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 10340Sodium CarbonateHCID 763102-Aminoindane

Product 1

HCID 12452137N-(2,3-Dihydro-1H-inden-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled mixture of 2-aminoindan (1.2 mol, 160.00 g) in ethyl acetate (1019 mL) at about 5-7° C. was added a solution of Na2CO3 (2.4 mol, 254.65 g) in water (1528 mL) while stirring, followed by the addition of a solution of acetyl chloride (1.32 mol, 109.19 g) slowly over 2 hours. The reaction temperature was maintained below 10° C. by adjusting the addition rate. During the addition, a suspension was formed. After the addition of acetyl chloride, the mixture was stirred at the room temperature for 1 hour. The precipitated solid was collected by vacuum filtration and the filter cake was washed with water (200 mL), EtOAc (200 mL), and air-dried for 48 hours. The first crop of the product was obtained as a white crystalline solid.

Workup

  1. temperatureThe reaction temperature was maintained below 10° C.
  2. additionDuring the addition
  3. customa suspension was formed
  4. stirringthe mixture was stirred at the room temperature for 1 hour
  5. filtrationThe precipitated solid was collected by vacuum filtration
  6. washthe filter cake was washed with water (200 mL), EtOAc (200 mL)
  7. customair-dried for 48 hours
  8. customThe first crop of the product was obtained as a white crystalline solid

Sources & evidence

ORD record
ord-4f26fd1225b948d6be339ae68764791b
Source dataset
uspto-grants-2009_08
Patent number
US07576238B2

Reaction notes

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