Dimethylformamide → 8-Methoxy-2-methyl-2,3,4,5-tetrahydro-benzo[c]azepin-1-one

HRID 1040642

反応式

HRID 1040642 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][NH:9][C:8](=[O:13])[C:7]=2[CH:14]=1.[H-].[Na+].[CH3:17]N(C=O)C>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][N:9]([CH3:17])[C:8](=[O:13])[C:7]=2[CH:14]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 112755298-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-one

生成物 1

HCID 672645628-Methoxy-2-methyl-2,3,4,5-tetrahydro-benzo[c]azepin-1-one

実験手順

A mixture of 8-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-one (283 mgs, 1.48 mmol) in DMF (5 mL) was treated with NaH (60% dispersion in mineral oil, 75 mgs, 1.85 mmol) and stirred for 10 min. The mixture was quenched with water and extracted with ether. The organic layers were washed with brine and the organic layer dried (MgSO4), filtered and concentrated to give 8-Methoxy-2-methyl-2,3,4,5-tetrahydro-benzo[c]azepin-1-one (227 mgs). 1H-NMR (CDCl3) δ 7.14 (d, J=2.7 Hz, 1H), 6.96 (d, J=8.1 Hz, 1H), 6.83-6.81 (m, 1H), 3.74 (s, 3H), 3.14 (t, J=6.6 Hz, 2H), 3.10 (s, 3H), 2.64 (t, J=8.1 Hz, 2H), 1.97-1.91 (m, 2H); LC/MS (ESI+): 273 (M+H).

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with ether
  3. washThe organic layers were washed with brine
  4. dry with materialthe organic layer dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-e51a1c56b3584e009df86d8bad6ae1cd
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

関連ノート

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