Acetyl chloride → N-(5-acetyl-2-methyl-indan-2-yl)-benzamide

HRID 562836Notes

Reaction equation

HRID 562836 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1.[C:24](Cl)(=[O:26])[CH3:25]>[N+](C)([O-])=O>[C:24]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[CH2:14][C:6]([NH:15][C:16](=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:5])[CH2:7]2)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22499247N-(2-methyl-indan-2-yl)-benzamide

Product 1

HCID 22499217N-(5-acetyl-2-methyl-indan-2-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Aluminium chloride (3.7 g) is dissolved in nitromethane (12 ml) under nitrogen followed by N-(2-methyl-indan-2-yl)-benzamide (3.0 g) at 0° C. Acetyl chloride (0.85 ml) is added dropwise over 30 minutes. After 4 hours at room temperature the mixture is quenched with ice and concentrated HCl, extracted with DCM. The organic layers are washed with dilute HCl and brine. Evaporation of the solvent yielded the desired product. ES+MS m/e 294 (MH+)

Workup

  1. customAfter 4 hours at room temperature the mixture is quenched with ice and concentrated HCl
  2. extractionextracted with DCM
  3. washThe organic layers are washed with dilute HCl and brine
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-784ff5237b1f4968916b160db1fb5d1c
Source dataset
uspto-grants-2011_11
Patent number
US08067437B2

Reaction notes

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