p-Fluoronitrobenzene → 4-nitro-N-prop-2-ynylaniline

HRID 1722707Notes

Reaction equation

HRID 1722707 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([NH2:14])[C:12]#[CH:13].[F-].[K+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:14][CH2:11][C:12]#[CH:13])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 239041PropargylamineHCID 522689Potassium Fluoride

Product 1

HCID 42148374-nitro-N-prop-2-ynylanilineYield 49%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 26.6 g (189 mmol) of 4-fluoronitrobenzene, 20.8 g (377 mmol) of propargylamine, 11 g (189 mmol) of potassium fluoride, and 26 g (188 mmol) of potassium carbonate in 600 ml of dimethylsulfoxide is stirred at room temperature under a nitrogen atmosphere for twenty hours. The reaction mixture is poured into 1.5 l of water and stirred at room temperature for two hours. The yellow solid is filtered, rinsed with water, and then isopropyl alcohol. The product is dried in vacuo at 50° C. for two days to give 16.27 g (49%) 4-nitro-N-2-propynylbenzenamine; mp 150°-153° C.

Workup

  1. stirringstirred at room temperature for two hours
  2. filtrationThe yellow solid is filtered
  3. washrinsed with water
  4. customThe product is dried in vacuo at 50° C. for two days

Sources & evidence

ORD record
ord-b491472baee24e0698b0241c97fc805e
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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