Methyl iodide → 1-Methyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

HRID 1686945ノート

反応式

HRID 1686945 の反応式
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[C:15](=O)([O-])[O-].[K+].[K+].IC.[H-].[Na+]>CN(C=O)C>[CH3:15][N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:14]=[CH:13][C:7]1=2

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 158877537-Nitro-2,3,4,5-tetrahydro-1H-benzo[B]azepine

生成物 1

HCID 672643011-Methyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 7-Nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (192 mg, 1.0 mmol) in DMF (10 mL) was treated with potassium carbonate (345 mg, 2.5 eq), and iodomethane (0.08 mL, 1.25 eq) and stirred at room temperature for 30 min. Sodium hydride was added (1.5 eq) and the mixture stirred for 30 min, quenched with water and extracted with ether. The organic layers washed with brine and dried (MgSO4), filtered and concentrated to give 1-Methyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (206 mg, 100%) as a yellow solid. MP: 52-54° C.; 1H-NMR (CDCl3) δ 7.97 (s, 1H), 7.89 (dd, J=2.6, 8.7 Hz, 1H), 6.61 (d, J=8.7 Hz, 1H), 4.42 (br s, 1H), 2.88-2.84 (m, 2H), 1.89-1.78 (m, 4H); LC/MS (ESI+): 207.04 (M+H).

後処理

  1. stirringthe mixture stirred for 30 min
  2. customquenched with water
  3. extractionextracted with ether
  4. washThe organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-000b780be1ad4049ac4745156831cb34
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

反応ノート

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