Sodium Hydroxide → 7-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 2174711Notes

Reaction equation

HRID 2174711 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([O:19][CH3:20])[C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>C1COCC1>[CH3:20][O:19][C:13]1[C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH2:10][C:9]=2[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866338662,2,2-Trifluoro-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone

Product 1

HCID 672643517-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.30 g (4.08 mmol) 2,2,2-trifluoro-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone and 3.06 ml (6.13 mmol) 2 molar sodium hydroxide solution are dissolved in 20 ml THF at room temperature and stirred for 3 h. Then the mixture is concentrated by evaporation i.vac., diluted with water and extracted with tert.-butyl-methylether. The organic phase is washed with 50% sodium hydroxide solution and sat. NaCl solution, dried on sodium sulphate and concentrated by evaporation i.vac.

Workup

  1. concentrationThen the mixture is concentrated by evaporation i.vac
  2. addition, diluted with water
  3. extractionextracted with tert.-butyl-methylether
  4. washThe organic phase is washed with 50% sodium hydroxide solution and sat. NaCl solution
  5. customdried on sodium sulphate
  6. concentrationconcentrated by evaporation i.vac

Sources & evidence

ORD record
ord-7ab8be3c8c9c44ce8007e9931491c66d
Source dataset
uspto-grants-2015_06
Patent number
US09062034B2

Reaction notes

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