Methyl iodide → 1-methyl-8-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 1586921Notes

Reaction equation

[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][C:11](=[O:13])[NH:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:18]I>CN(C)C=O>[CH3:18][N:12]1[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:15]=[CH:14][C:7]=2[CH2:8][CH2:9][CH2:10][C:11]1=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

2.58 g of 2,3,4,5-tetrahydro-8-nitro-2-oxo-1H-1-benzazepine dissolved in 30 ml of abs. dimethylformamide were added to 650 mg of 55% NaH in 20 ml of abs. dimethylformamide. The mixture was stirred for 1 hour, then cooled to 0° C. and 1.35 ml of methyl iodide were slowly added dropwise thereto. After 45 minutes the mixture was poured on ice, extracted with ethyl acetate, washed with NaCl solution, dried and evaporated. Flash chromatography on silica gel (hexane/ethyl acetate=1/1) yielded 2.46 g of 2,3,4,5-tetrahydro-1-methyl-8-nitro-2-oxo-1H-1-benzazepine as orange crystals of m.p. 151°-152° C.

Workup

additionAfter 45 minutes the mixture was poured on ice
extractionextracted with ethyl acetate
washwashed with NaCl solution
customdried
customevaporated

Sources & evidence

ORD record: ord-289dad2dbe8d4fbdbf1c8cba898583e9
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05216148

Reaction notes

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