Potassium Carbonate → 3-(3-Benzyloxy-4-nitrophenoxy)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

HRID 660768Notes

Reaction equation

HRID 660768 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:18])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:20]1[C:26](=[O:27])[NH:25][C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[O:18][CH:20]1[C:26](=[O:27])[NH:25][C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[CH2:22][CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27571843-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 109777113-(Benzyloxy)-4-nitrophenol

Product 1

HCID 688395523-(3-Benzyloxy-4-nitrophenoxy)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-benzyloxy-4-nitrophenol (2.45 g, 10 mmol), 3-bromo-1,3,4,5-tetrahydrobenzo[b]azepin-2-one (2.4 g, 10 mmol) and potassium carbonate (3.1 g, 23 mmol) in MeCN (10 mL) is refluxed for 10 h. Upon cooling a precipitate forms. The solid is filtered, washed with water and crystallized from EtOAc to give the title compound: mp=188-189° C.

Workup

  1. temperatureis refluxed for 10 h
  2. temperatureUpon cooling a precipitate forms
  3. filtrationThe solid is filtered
  4. washwashed with water
  5. customcrystallized from EtOAc

Sources & evidence

ORD record
ord-33d4ea35e13b4a1eaaef8144c5f2afdf
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…