p-Anisoyl chloride → 4-methoxy-N-(1-oxo-indan-5-yl)-benzamide

HRID 1766316Notes

Reaction equation

HRID 1766316 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[C:12](Cl)(=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C(N(CC)CC)C>C1COCC1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)=[O:21])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 3128905-amino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 211103044-methoxy-N-(1-oxo-indan-5-yl)-benzamideYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 5-amino-indan-1-one (73 mg, 0.50 mmol) in THF (6 mL) with p-anisoyl chloride (88 μL, 0.65 mmol) in presence of triethylamine (90 μL, 0.65 mmol) according to method A gave 4-methoxy-N-(1-oxo-indan-5-yl)-benzamide (107 mg, 0.38 mmol, 76% yield) as a yellow powder after purification by chromatography on silica gel (eluent EtOAc/DCM 0/10 to 2/8).

Sources & evidence

ORD record
ord-cffcebc04bf045eeae000b1f7ebece0c
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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