Iodoethane → HCID 67264711, compound

HRID 1487206Notes

Reaction equation

HRID 1487206 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9](=[O:14])[NH:8][C:7]=2[CH:6]=[CH:5][C:4]=1[N+:15]([O-:17])=[O:16].[H-].[Na+].[CH2:20](I)[CH3:21]>CN(C)C=O>[CH2:20]([N:8]1[C:9](=[O:14])[CH2:10][CH2:11][CH2:12][C:13]2[C:3]([O:2][CH3:1])=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]1=2)[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 57853800HCID 57853800, compound

Product 1

HCID 67264711HCID 67264711, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-methoxy-7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (4.5 g, 19.0 mmol) in dimethylformamide (30 mL) at 0° C. was added sodium hydride (60% on mineral oil, 1.15 g, 28.5 mmol) in small portions within 30 minutes. The mixture was stirred for 30 minutes at this temperature followed by adding ethyl iodide (1.84 mL, 22.9 mmol) dropwise. The mixture was warmed to room temperature and stirred for another 2 hours. Upon completion, the mixture was poured into ice-water and filtered to afford the product 1-ethyl-6-methoxy-7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one as a off-white solid (3.77 g, yield 78.5%). 1H NMR (400 MHz, CDCl3) δ ppm 7.81-7.84 (dd, 1H, J=1.6 Hz, 8.8 Hz), 7.08-7.10 (dd, 1H, J=1.2 Hz, 8.8 Hz), 3.76-3.94 (s+m, 5H), 2.89-2.96 (m, 2H), 2.22-2.32 (m, 4H), 1.16-1.26 (m, 3H).

Workup

  1. stirringstirred for another 2 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-c16b3a925deb4625887046c222841075
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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