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

HRID 1040642노트

반응식

HRID 1040642 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e51a1c56b3584e009df86d8bad6ae1cd
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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