Triethylamine → ethyl 3-(N-(4-(3-furanyl)-2-nitrophenyl))aminobenzoate

HRID 324747Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][CH:9]=2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH2:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)CC)C>CN1C(=O)CCC1>[O:10]1[CH:11]=[CH:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:16][C:17]3[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=3)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=2)=[CH:9]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1d (2.07 g, 10 mmol) in NMP (2 ml) was added ethyl 3-aminobenzoate (1.82 g, 11 mmol) and triethylamine and the mixture was heated to 110° C. in a nitrogen atmosphere overnight. The mixture was diluted with ice-water and extracted with ethyl acetate . The concentrated extract was purified by column-chromatography on silica gel using a mixture of petroleum ether and ethyl acetate (9:1 v/v) to yield ethyl 3-(N-(4-(3-furanyl)-2-nitrophenyl))aminobenzoate (1.18 g, 34%). This ester was hydrogenated in ethanol at ambient pressure using Pd (5% on activated carbon) as the catalyst. The resulting diamine (1.07 g) was treated with triethyl orthoformate (1.11 ml, 6.64 mmol) and a catalytic amount of pTSA in refluxing THF (10 ml). Column-chromatographic work-up of the concentrated reaction mixture using ethyl acetate as the eluent afforded 6c1 (0.66 g, 56%). M.p. 87-89° C.

Workup

extractionextracted with ethyl acetate
extractionThe concentrated extract
customwas purified by column-chromatography on silica gel using
additiona mixture of petroleum ether and ethyl acetate (9:1 v/v)

Sources & evidence

ORD record: ord-ef9645b245ad4060af67d96bb209a3ec
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218547B1

Reaction notes

Loading…