Triethylamine → 3-methoxy-N-(1-oxo-indan-5-yl)-benzamide

HRID 1766317Notes

Reaction equation

HRID 1766317 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][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.C(N(CC)CC)C>C1COCC1>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[C:12]([NH: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)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 3128905-amino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 211103013-methoxy-N-(1-oxo-indan-5-yl)-benzamideYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 5-amino-indan-1-one (73 mg, 0.50 mmol) in THF (6 mL) with m-anisoyl chloride (90 μL, 0.65 mmol) in presence of triethylamine (90 μL, 0.65 mmol) according to method A gave 3-methoxy-N-(1-oxo-indan-5-yl)-benzamide (73 mg, 0.26 mmol, 52% yield) as a yellow powder after purification by chromatography on silica gel (eluent EtOAc/DCM 0/10 to 1/9).

Sources & evidence

ORD record
ord-d076014d887743eda30f98249ed6a422
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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