Acryloyl chloride → HCID 59442105, compound

HRID 1014278Notes

Reaction equation

HRID 1014278 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2.[CH:15]([N:18]([CH:21]([CH3:23])C)[CH2:19]C)(C)C.[C:24](Cl)(=[O:27])C=C>ClCCl.CNC.O1CCCC1>[CH3:19][N:18]([CH3:15])[CH2:21][CH2:23][C:24]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:6][CH2:7]1)=[O:27]

Participants

7

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 59442105HCID 59442105, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 674DimethylamineSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-(methyloxy)-6-nitro-2,3-dihydro-1 H-indole (1.50 g, 7.73 mmol) and polymer supported diisopropylethylamine (4.1 g, 16 mmol) in dichloromethane (100 mL) was cooled to 0° C. and 2-propenoyl chloride (0.750 mL, 9.3 mmol) was added dropwise. The solution was warmed slowly to room temperature and all solids were observed to dissolve. The mixture was filtered through celite, the celite washed twice with dichloromethane, and the combined filtrates were concentrated under reduced pressure to give a crude residue which was dissolved directly in a 1.0M dimethyl amine solution in tetrahydrofuran (40 mL). The solution was maintained at 60° C. for 12 hours, cooled, taken to a residue under reduced pressure, and purified by chromatography on SiO2 to afford N,N-dimethyl-3-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-3-oxo-1-propanamine (1.52 g, 67% Yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.68 (s, 1 H), 6.91 (s, 1 H), 4.15 (t, J=8.43 Hz, 2 H), 3.91 (s, 3 H), 3.26 (t, J=8.43 Hz, 2 H), 2.81 (t, J=7.33 Hz, 2 H), 2.66 (t, J=7.15 Hz 2 H), 2.27-2.41 (m, 6H). U24644/64/1

Workup

  1. temperatureThe solution was warmed slowly to room temperature
  2. dissolutionto dissolve
  3. filtrationThe mixture was filtered through celite
  4. washthe celite washed twice with dichloromethane
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. customto give a crude residue which
  7. temperatureThe solution was maintained at 60° C. for 12 hours
  8. temperaturecooled
  9. custompurified by chromatography on SiO2

Sources & evidence

ORD record
ord-2856431d9d7d4a1eac07df3308104236
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…