Water → 2-Nitro-4-(2-naphthyl)aniline

HRID 1479119Notes

Reaction equation

HRID 1479119 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:1]([C:4]1[CH:10]=[C:9]([C:14]2[CH:13]=[CH:12][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 701324-Bromo-2-nitroanilineHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 106830162-Nitro-4-(2-naphthyl)anilineYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 2-nitro-4-bromoaniline (5 g, 23 mmol) in toluene is admixed with 3.27 g (23 mmol) of 2-naphthylboronic acid, 9.5 g (0.069 mol) of potassium carbonate and 1.3 g of tetrakis(triphenylphosphine)palladium. The mixture is heated to reflux for 4 hours and the reaction is stopped by adding 100 ml of water. The mixture is extracted with ethyl acetate and dried over sodium sulphate, and the solvent is removed under reduced pressure. Purification by column chromatography gives 4.1 g (68% yield).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 4 hours
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is removed under reduced pressure
  6. customPurification by column chromatography
  7. customgives 4.1 g (68% yield)

Sources & evidence

ORD record
ord-38008440dea04738bc60abe191106a20
Source dataset
uspto-grants-2016_08
Patent number
US09406848B2

Reaction notes

Loading…