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

HRID 1040637ノート

反応式

HRID 1040637 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-000c242180f04f35a0c2185260cf8469
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

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