Dimethylformamide → 1-[6-(N-tert-Butoxycarbonylamino)-1-hexyl]-4-[2-hydroxy-1-ethylcarbamoyl]-1,2-dihydroquinoline-2-one

HRID 555328Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([OH:17])[CH:8]=1)=[O:6].[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([C:5](=[O:6])[NH:4][CH2:3][CH2:2][OH:1])=[CH:8][C:9]1=[O:17])=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(2-hydroxy-1-ethylcarbamoyl)-2-hydroxyquinoline (1.2 g), N-(tert-butoxycarbonyl)-6-bromo-hexylamine (2.2 g), cesium carbonate (4 g) and N,N-dimethylformamide (50 ml) was stirred for 6 hours at 60° C. followed by stirring overnight at room temperature. Ice and water were added and the mixture was extracted three times with ethyl acetate. The organic phases were washed with saturated sodium chloride, dried and evaporated to leave a yellow oil which after purification by chromatography on silica gel with ethyl acetate/methanol/aqueous ammonia (45:5:1.5) as eluent gave the desired compound as a light brown solid.

Workup

stirringby stirring overnight at room temperature
extractionthe mixture was extracted three times with ethyl acetate
washThe organic phases were washed with saturated sodium chloride
customdried
customevaporated
customto leave a yellow oil which
customafter purification by chromatography on silica gel with ethyl acetate/methanol/aqueous ammonia (45:5:1.5) as eluent

Sources & evidence

ORD record: ord-37a02f99d706459192210c7d00f960bf
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053446B2

Reaction notes

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