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

HRID 1686950Notes

Reaction equation

HRID 1686950 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ecc838cf9f0d4184a7b73a78cfaaca2a
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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