Sodium Hydroxide → 4-Amino-4'-methoxystilbene

HRID 1823046Notes

Reaction equation

HRID 1823046 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[Sn].[OH-].[Na+]>C(O)C.Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 745105(E)-1-Methoxy-4-(2-(4-nitrophenyl)ethenyl)benzeneHCID 5352426Tin atom

Product 1

HCID 53764914-Amino-4'-methoxystilbeneYield 69%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 10.1 g (40 mmol) of (E)-1-methoxy-4-[2-(4-nitrophenyl)ethenyl]-benzene in 70 ml of ethanol and 130 ml of hydrochloric acid (25%) is heated to 110° C. Portionwise, 15 g of tin are added and stirring is continued for 4.5 hours at 110° C. For the working-up, the reaction mixture is cooled and neutralised with a solution of sodium hydroxide. The mixture is transferred to a separatory funnel where it is extracted with dichloromethane. The organic layer is separated, dried over sodium sulfate and evaporated. The residue is triturated in ether and, thereafter, the remaining solid is collected on a filter funnel. There are obtained 6.15 g (69% of theory) of (E)-4-[2-(4-methoxy-phenyl)-vinyl]-phenylamine as a yellow crystals; MS: m/e=226 (M+H)+.

Workup

  1. temperaturethe reaction mixture is cooled
  2. customThe mixture is transferred to a separatory funnel
  3. extractionwhere it is extracted with dichloromethane
  4. customThe organic layer is separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is triturated in ether
  8. customthe remaining solid is collected on a filter funnel

Sources & evidence

ORD record
ord-d7771714b93c417899b51b0f0469ed5c
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

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