Sodium hydride → 1-(2-Methoxy-ethyl)-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

HRID 1687153Notes

Reaction equation

HRID 1687153 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[NH:8][C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].BrC[CH2:20][CH2:21][O:22][CH3:23]>CN(C=O)C>[CH3:23][O:22][CH2:21][CH2:20][N:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:15]=[CH:14][C:7]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3561757-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-oneHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 672641631-(2-Methoxy-ethyl)-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one solid (566.6 mg, 2.75 mmol) in DMF (5 mL) was added NaH (200 mg, 60% dispersion in mineral oil, 5.0 mmol). After stirring for 15 min, 1-bromo-3-methoxy-propane (764 mg, 5.5 mmol) was added and the mixture stirred at room temperature for 1 hour prior to quenching with 10% aqueous NH4Cl solution. Solvent was removed by rotary evaporation and the residue extracted into EtOAc, washed with water (2×), brine and dried by passing through a plug of MgSO4. The resulting filtrate was evaporated onto Florisil and purified by chromatography (silica gel, DCM→15% EtOAc/DCM gradient). The appropriate fractions were combined and evaporated to afford 1-(2-methoxy-ethyl)-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as an oil that was carried onto the next step.

Workup

  1. stirringthe mixture stirred at room temperature for 1 hour
  2. customto quenching with 10% aqueous NH4Cl solution
  3. customSolvent was removed by rotary evaporation
  4. extractionthe residue extracted into EtOAc
  5. washwashed with water (2×), brine
  6. customdried
  7. customThe resulting filtrate was evaporated onto Florisil
  8. custompurified by chromatography (silica gel, DCM→15% EtOAc/DCM gradient)
  9. customevaporated

Sources & evidence

ORD record
ord-a72639c6dc9749f1a2327851d14cd918
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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