Pyridine → N-(Phenylmethyl)-9H-fluorene-9-carboxamide

HRID 993466Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([C:14]([OH:16])=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C.O>[C:24]1([CH2:23][NH:30][C:14]([CH:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[O:16])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 9-fluorene carboxylic acid (2.10 g, 10.0 mmol) in 50 mL of CH2Cl2 was treated with oxalyl chloride in dichloromethane (6.0 mL, 12.0 mmol) and two drops of DMF. After 0.75 h, the mixture was concentrated under reduced pressure to give a white solid. The solid was diluted with 50 mL of CH2Cl2, cooled to 0° C., treated with benzylamine (1.17 g, 11.0 mmol) and pyridine (0.87 g, 11 mmol). The transparent yellow solution was stirred for 3 h at room temperature and diluted with ethyl acetate and water. The organic fraction was dried over Na2SO4 and concentrated to a white solid. The solid purified by trituration with hexanes and recrystalization from hot methanol to give 2.60 g (86%) of title compound as white flakes. mp 195-200° C.

Workup

concentrationthe mixture was concentrated under reduced pressure
customto give a white solid
dry with materialThe organic fraction was dried over Na2SO4
concentrationconcentrated to a white solid
customThe solid purified by trituration with hexanes and recrystalization from hot methanol

Sources & evidence

ORD record: ord-7f2a6890c0294946aced46aa357ce3d3
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472414B1

Reaction notes

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