2-(4-Aminophenyl)ethylamine → HCID 66796133, compound

HRID 1670800Notes

Reaction equation

HRID 1670800 reaction equation
Br[CH2:2][CH:3]([C:12]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:30])[NH:17]2)[O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][NH2:40])=[CH:34][CH:33]=1>CS(C)=O.C(OCC)(=O)C>[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][NH:40][CH2:2][C@@H:3]([C:12]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16](=[O:30])[NH:17]3)[O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6])=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 728952-(4-Aminophenyl)ethylamineHCID 218806418-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]quinolin-2(1H)-one

Product 1

HCID 66796133HCID 66796133, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(2-bromo-1-(tert-butyl-dimethyl-silanyloxy)-ethyl)-8-benzyloxy-1H-quinolin-2-one (5.0 g, 1.0 equiv) and 2-(4-aminophenyl)ethylamine (2.8 g, 2.0 equiv) in dimethylsulfoxide (10 mL) was heated at 100° C. for 12 h. The reaction mixture was cooled to 20° C., and the resulting red oil was diluted with ethyl acetate (200 mL) and extracted with two portions water (200 mL). The organic layer was washed with two portions of (1:1 10% aqueous acetic acid and saturated aqueous sodium chloride (200 mL). The organic layer was basified by carefully extracting with two portions of saturated sodium bicarbonate (200 mL), followed by saturated sodium chloride (200 mL). The resulting organic solution was treated with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to afford the title intermediate (5.1 g) which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 20° C.
  2. extractionextracted with two portions water (200 mL)
  3. washThe organic layer was washed with two portions of (1:1 10% aqueous acetic acid and saturated aqueous sodium chloride (200 mL)
  4. extractionby carefully extracting with two portions of saturated sodium bicarbonate (200 mL)
  5. additionThe resulting organic solution was treated with anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-84e5f108cc274240a2acd3e7e5874f29
Source dataset
uspto-grants-2011_08
Patent number
US07994165B2

Reaction notes

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