Nitromethane → (2z)-2-(Nitromethylene)-2,3,4,5-tetrahydro-1h-1-benzazepine

HRID 80529Notes

Reaction equation

HRID 80529 reaction equation
CS[C:3]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[N:4]=1.[N+:14]([CH3:17])([O-:16])=[O:15]>>[N+:14](/[CH:17]=[C:3]1\[NH:4][C:5]2[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=2[CH2:7][CH2:8][CH2:9]\1)([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 6375NitromethaneHCID 125454282-(Methylthio)-4,5-dihydro-3h-1-benzazepine

Product 1

HCID 13842538(2z)-2-(Nitromethylene)-2,3,4,5-tetrahydro-1h-1-benzazepine

Procedure

A mixture of Example 182C (2.481 g, 12.97 mmol) and nitromethane (13.99 mL, 259 mmol) was heated with an oil bath at 120° C. for 48 hours. The nitromethane was evaporated and the crude mixture was purified by silica gel chromatography (Analogix IntelliFlash™280, SF25-80) eluting with 15-30% ethyl acetate/hexanes to obtain the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 11.15 (s, 1H), 7.34-7.25 (m, 3H), 7.25-7.15 (m, 1H), 6.87 (s, 1H), 2.77-2.64 (m, 2H), 2.22 (m, 2H), 2.14 (m, 2H); MS (ESI+) m/z 205.3 (M+H)+.

Workup

  1. customThe nitromethane was evaporated
  2. customthe crude mixture was purified by silica gel chromatography (Analogix IntelliFlash™280, SF25-80)
  3. washeluting with 15-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-dc8ecf5634464e5eaaef66b563df4928
Source dataset
uspto-grants-2014_09
Patent number
US08846663B2

Reaction notes

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