8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one → HCID 16244477, compound

HRID 2173670Notes

Reaction equation

HRID 2173670 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9](=O)[NH:8][C:7]=2[CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:7]=2[CH:14]=1

Participants

4

Reactant 2

HCID 6769538-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 16244477HCID 16244477, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (2 g) in THF (100 mL), lithium aluminum hydride (0.79 g) was added, and the reaction heated to reflux. After stirring for 1 hour, the heat was removed. Water (6 mL) was added followed by NaOH (10%, 15 mL), the flocculated solids removed by filtration, and the eluent concentrated to provide the title compound (1.9 g) as a pale brown oil: 1H NMR (DMSO-d6) δ 6.88 (d, 1H); 6.37 (d, 1H), 6.22 (dd, 1H), 5.14 (s, 1H), 3.62 (s, 3H), 2.90-2.85 (m, 2H), 2.57-2.53 (m, 2H), 1.67-1.59 (m, 2H), 1.52-1.45 (m, 2H).

Workup

  1. temperaturethe reaction heated to reflux
  2. customthe heat was removed
  3. additionWater (6 mL) was added
  4. customthe flocculated solids removed by filtration
  5. concentrationthe eluent concentrated

Sources & evidence

ORD record
ord-04add02dc26345409c7db4159e56c6b7
Source dataset
uspto-grants-2015_06
Patent number
US09056885B2

Reaction notes

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