Benzoyl chloride → N-(1-methyl-3-oxo-indan-5-yl)benzamide

HRID 593266

Reaction equation

HRID 593266 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][CH:11]1[C:19]2[C:14](=[CH:15][C:16]([N+:20]([O-])=O)=[CH:17][CH:18]=2)[C:13](=[O:23])[CH2:12]1.C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[CH3:10][CH:11]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:17][CH:18]=2)[C:13](=[O:23])[CH2:12]1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 6007023-methyl-6-nitro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 86703337N-(1-methyl-3-oxo-indan-5-yl)benzamideYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

As presented in the following reaction formula, a solution of benzoyl chloride (PhCOCl; 6.7 g, 0.043 mol) in dichloromethane (DCM; 20 mL) was added at 0° C. to a mixture of 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one (7 g, 0.043 mol) and triethylamine (9.6 g, 0.095 mol) in dichloromethane (DCM; 100 mL), and the reaction mixture was stirred for 2 hours. After the completion of reaction, the mixture was washed with water (50 mL), saturated sodium hydrogen carbonate (50 mL) and saturated brine (50 mL) and then concentrated to give a crude product. The crude product was purified by silica gel (50 g) column chromatography (product of Merck Co., Ltd.) using an eluent of pentane (PE):ethyl acetate (10:1 (by volume)) to give the desired product N-(1-methyl-3-oxo-indan-5-yl)benzamide (10 g, yield: 87%) as a yellow solid.

Workup

  1. customAfter the completion of reaction
  2. washthe mixture was washed with water (50 mL), saturated sodium hydrogen carbonate (50 mL) and saturated brine (50 mL)
  3. concentrationconcentrated
  4. customto give a crude product
  5. customThe crude product was purified by silica gel (50 g) column chromatography (product of Merck Co., Ltd.)

Sources & evidence

ORD record
ord-5feabcee308f439686424084a76a7a3a
Source dataset
uspto-grants-2016_01
Patent number
US09242928B2

Linked notes

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