Dimethylamine → 2-(Dimethylamino)-1-(5-methoxy-6-nitroindolin-1-yl)ethanone

HRID 1014252Notes

Reaction equation

HRID 1014252 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](C)C)[CH2:19]C)(C)[CH3:16].BrCC(Cl)=[O:27].CNC.O1CCCC1>ClCCl>[CH3:19][N:18]([CH3:21])[CH2:15][C:16]([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 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 594418292-(Dimethylamino)-1-(5-methoxy-6-nitroindolin-1-yl)ethanoneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (1.00 g, 5.2 mmol) in dichloromethane (50 mL) was added polymer supported diisopropylethylamine (Argonaut Technologies Inc., 4.0 g, ca 15 mmol base) and bromoacetylchloride (0.650 mL, 7.82 mmol). The resulting solution was stirred for three hours and filtered through a plug of celite. Dichloromethane was removed under reduced pressure and the residue was dissolved in tetrahydrofuran (50 mL). To the solution was added dimethylamine as a 2.0M solution in tetrahydrofuran (60 mmol, Aldrich) and the resulting solution was stirred overnight. The next morning the volatiles were removed under reduced pressure and the residue was purified via chromatography on SiO2 (0-10% MeOH/CH2CL2 with 0.2% NH3) to afford N,N-dimethyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine as a yellow solid (1.20 g, 4.33 mmol, 84% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.59 (s, 6 H), 3.24 (t, J=8.24 Hz, 2 H), 3.52 (s, 2 H), 3.89 (s, 3 H), 4.19 (t, J=8.52 Hz, 2 H), 6.89 (s, 1 H), 8.60 (s, 1 H).

Workup

  1. filtrationfiltered through a plug of celite
  2. customDichloromethane was removed under reduced pressure
  3. dissolutionthe residue was dissolved in tetrahydrofuran (50 mL)
  4. stirringthe resulting solution was stirred overnight
  5. customThe next morning the volatiles were removed under reduced pressure
  6. customthe residue was purified via chromatography on SiO2 (0-10% MeOH/CH2CL2 with 0.2% NH3)

Sources & evidence

ORD record
ord-0f83e173f3e14b7a8df6d8f1b6740442
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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