Water → HCID 66987879, compound
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].[C:14]([O:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)=[O:20])([CH3:17])([CH3:16])[CH3:15].O>CN(C)C=O>[C:14]([O:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]1=[O:1])=[O:20])([CH3:17])([CH3:16])[CH3:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
2-Hydroxyquinoline (640 mg) was added to a suspension of 600% sodium hydride (205 mg) in N,N-dimethylformamide (15 ml) and the mixture was stirred at 60° C. for 30 minutes. After cooling in ice a solution of N-(tert-butoxycarbonyl)-6-bromo-hexylamine (1.25 g) (Helv. Chim. Acta 76 891 (1993)) in N,N-dimethylformamide (10 ml) was added dropwise and stirring was continued 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 as eluent gave the desired compound as a colourless oil.
Workup
- additionwas added dropwise
- stirringstirring
- waitwas continued 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 as eluent
Sources & evidence
- ORD record
- ord-49350ec7d29c4eb0a049b2b4bf04bf25
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053446B2
Reaction notes
Loading…