Sodium Hydroxide → 7-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepine

HRID 1668579Notes

Reaction equation

HRID 1668579 reaction equation
C([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>Cl>[N+:15]([C:13]1[CH:12]=[CH:11][C:8]2[CH2:9][CH2:10][NH:4][CH2:5][CH2:6][C:7]=2[CH:14]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 218229223-acetyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 113100427-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepineYield 97.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-acetyl-7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine (2.9 g) in HCl (conc) (200 ml) as refluxed for 48 h. Mixture was cooled at 0° C. and neutralised with NaOH (conc.) then was extracted with DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were concentrated to provide the target compound (2.33 g).

Workup

  1. extractionthen was extracted with DCM
  2. customThe organic layer was collected
  3. extractionthe aqueous phase extracted twice with DCM
  4. concentrationThe combined DCM layers were concentrated

Sources & evidence

ORD record
ord-c0ed2807c13643c59a4af558f878498d
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

Loading…