Toluene → 3-(6H-Dibenzo[b,e]oxepin-1-ylidenemethyl)-phenylamine

HRID 2218732Notes

Reaction equation

HRID 2218732 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[CH:7]=[C:8]1O[C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[CH2:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)([O-])=O.[OH2:26].O.[Sn](Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>C(O)C.C(OCC)(=O)C>[C:8]1(=[CH:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:25]=[CH:24][CH:23]=2)[C:9]2[C:22]([O:26][CH2:13][C:15]3[CH:16]=[CH:17][CH:18]=[CH:12][C:11]=3[CH:10]=2)=[CH:21][CH:20]=[CH:19]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 85782573Tin tetrachloride dihydrateHCID 866039843-Nitro-benzylidene-6,11-dihydro-dibenzo[b,e]oxepine

Product 1

HCID 866039833-(6H-Dibenzo[b,e]oxepin-1-ylidenemethyl)-phenylamineYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 11-(3-Nitro-benzylidene-6,11-dihydro-dibenzo[b,e]oxepine (200 mg) in ethanol (10 mL) add tin chloride dihydrate (680 mg) and reflux for 5 h. Concentrate the reaction in vacuo, re-dissolve in ethyl acetate and wash with 1N sodium hydroxide solution. Separate the layers wash with brine and dry over sodium sulfate. Purity using filter chromatography eluting with 10% ethyl acetate:toluene to give 60 mg of product (56% yield).

Workup

  1. temperaturereflux for 5 h
  2. concentrationConcentrate
  3. customthe reaction in vacuo
  4. washwash with 1N sodium hydroxide solution
  5. customSeparate the layers
  6. washwash with brine
  7. dry with materialdry over sodium sulfate
  8. filtrationPurity using filter chromatography
  9. washeluting with 10% ethyl acetate

Sources & evidence

ORD record
ord-2cffb80652e44e01aaa6a3839092257b
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

Loading…