N-Methylaniline → HCID 10219937, compound

HRID 1871019Notes

Reaction equation

HRID 1871019 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:11]([CH3:10])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 3

HCID 7515N-MethylanilineHCID 12162Benzonitrile, 4-bromo-HCID 83681Tris(1,1-dimethylethyl)phosphine

Product 1

HCID 10219937HCID 10219937, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

The above general procedure was followed using 4-bromobenzonitrile (187 mg, 1.00 mmol) and N-methylaniline (107 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.0 mL of toluene. After 6 hours, the reaction mixture was adsorbed onto silica gel and chromatographed with 10% ethyl acetate/hexanes to give 201 mg (97%) of N-(4-cyanophenyl)-N-methylaniline. 1H NMR (500 MHz, CDCl3) δ 7.45-7.42 (m, 4H), 7.27 (t, J=7.5 Hz, 1H), 7.21 (d, J=8.3 Hz, 2H), 6.73 (d, J=9.0 Hz, 2H), 3.36 (s, 3H). 13C NMR (125 MHz, CDCl3) δ 152.0, 146.8, 133.1, 130.1, 126.4, 126.2, 120.2, 114.0, 99.4, 40.1.

Workup

  1. customchromatographed with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e00c8815622c4001a39eb4452d58ac96
Source dataset
uspto-grants-2000_08
Patent number
US06100398

Reaction notes

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