1-Naphthalenecarbonyl chloride → HCID 19438806, compound

HRID 1733853Notes

Reaction equation

[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH3:12])=[O:2].[C:13]1([C:23](Cl)=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.O.CCOC(C)=O>CN(C=O)C.[H-].[Na+]>[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:23]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)=[O:24])[C:4]=1[CH3:12])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To 3-formyl-2-methylindole (4.30 g; 27.0 mmol) in 70 mL of DMF at r.t. was added NaH 80% (0.861 mg). After 30 min of stirring the solution was cooled to 0° C. and a solution of 1-naphthoyl chloride (5.04 g, 29.3 mmol) in 10 mL of DMF was added dropwise. The mixture was left stirring for 16 h at r.t. and poured into cold water-EtOAc (100mL). The organic phase was washed with H2O (2×25 mL) and brine. The organic phase was dried over Na2SO4 and the solvent removed. Chromatography on silica gel (eluted with 10% EtOAc in toluene) yielded 1.70 g (20%) of the title compound.

Workup

waitThe mixture was left
stirringstirring for 16 h at r.t.
washThe organic phase was washed with H2O (2×25 mL) and brine
dry with materialThe organic phase was dried over Na2SO4
customthe solvent removed

Sources & evidence

ORD record: ord-aa664bb09191439faf03cb8791b1bfea
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05532237

Reaction notes

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