Toluene → HCID 21940731, compound

HRID 1470794Notes

Reaction equation

HRID 1470794 reaction equation
[CH:1]1(P(C2CCCCC2)C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1.[OH-].[K+].CO[C:32]1[CH:33]=[C:34](Cl)[CH:35]=[C:36](OC)[CH:37]=1.[C:41]1([NH2:47])C=CC=CC=1.[C:48]1([CH3:54])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:32]1([N:47]([C:50]2[CH:51]=[C:52]([CH3:1])[CH:53]=[C:48]([CH3:54])[CH:49]=2)[CH3:41])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6115AnilineHCID 14797Potassium HydroxideHCID 815021-Chloro-3,5-dimethoxybenzeneHCID 53354804HCID 53354804, compound

Product 1

HCID 21940731HCID 21940731, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Under the protection of nitrogen, 0.05 equivalent of palladium acetate, 0.075 equivalent of dicyclohexyl(2,6-diisopropoxyphenyl)phosphine tetrafluoborate, 2.0 equivalent of potassium hydroxide, 1.0 equivalent of 3,5-dimethoxychlorobenzene and 1.2 equivalent of phenylamine were reacted in toluene at 110° C. for 3 hours. N-phenyl-N-methyl-3,5-dimethylphenylamine was obtained with a yield of 93%.

Sources & evidence

ORD record
ord-6acd0601f1a248399b9671434e77c5e0
Source dataset
uspto-grants-2015_04
Patent number
US09006491B2

Reaction notes

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