N-bromobutanimide → 1,1-dimethylethyl 6-bromo-7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 1668585Notes

Reaction equation

HRID 1668585 reaction equation
[OH:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C1C(=O)N([Br:30])C(=O)C1>C(Cl)Cl>[Br:30][C:3]1[C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=2[CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 589728117-Hydroxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester

Product 1

HCID 591505311,1-dimethylethyl 6-bromo-7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromination of 1,1-dimethylethyl 7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (71 mg) was performed with NBS (41 mg) in DCM (2.2 ml) and SiO2 (426 mg) at −15° C. under nitrogen. After 15 minutes SiO2 was filtered off and the solvent was evaporated under reduced pressure. The crude was purified on silica gel (ethyl acetate/petroleum ether, 1/9) obtaining the title compound as a yellow solid (72 mg).

Workup

  1. filtrationAfter 15 minutes SiO2 was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude was purified on silica gel (ethyl acetate/petroleum ether, 1/9)

Sources & evidence

ORD record
ord-f1a4aad038654991961622ddadc81474
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

Loading…