N-(4-Methoxybenzylidene)aniline → 1-Methoxy-4-(phenylethynyl)benzene

HRID 1492661Notes

Reaction equation

HRID 1492661 reaction equation
[C:1]1([CH2:7]N2C3C=CC=CC=3N=N2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=NC2C=CC=CC=2)=[CH:21][CH:20]=1>CO>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 98633N-(4-Methoxybenzylidene)anilineHCID 5212121-Benzyl-1H-benzotriazole

Product 1

HCID 6104021-Methoxy-4-(phenylethynyl)benzeneYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Procedure similar to that of Example 16 using [phenylmethyl]-1H-benzotriazole (10 mmol) and N-[(4-methoxyphenyl)methylene]benzenamine (10 mmol): 67% yield: mp 57°-58° C. (MeOH) (lit.1 58°-60° C.); 1H NMR (300 MHz, CDCl3) δ3.84 (s, 3H, OCH3), 6.89 (d, 1.9H, 2H, C(3 and 5)H), 7.30-7.38 (m, 3H), 7.45-7.54 (m, 4H).

Sources & evidence

ORD record
ord-2a4511c00ff646e29b5a83a5c0a371d1
Source dataset
uspto-grants-1994_12
Patent number
US05374701

Reaction notes

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