4-[(4-Methoxyphenyl)ethynyl]benzaldehyde → 6-({4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

HRID 551947Notes

Reaction equation

HRID 551947 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:28][C:27]([CH3:30])([CH3:29])[O:26][C:25](=[O:31])[C:24]=2[CH:32]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][NH:19][C:20]3[CH:21]=[CH:22][C:23]4[O:28][C:27]([CH3:29])([CH3:30])[O:26][C:25](=[O:31])[C:24]=4[CH:32]=3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 113338214-[(4-Methoxyphenyl)ethynyl]benzaldehydeHCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one

Product 1

HCID 575545066-({4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-oneYield 54%

Procedure

The title compound was prepared following procedure described in Example 1, step c) from 4-[(4-methoxyphenyl)ethynyl]benzaldehyde (1.31 g; 5.53 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) and 6-amino-2,2-dimethyl-benzo[1,3]dioxin-4-one (1.07 g; 5.53 mmol). The crude (1.7 g) was purified by recrystallisation from MeOH/EtOAc to give 1.23 g (54%) of the title compound as a yellow powder. HPLC, Rt: 4.77 min (purity: 77%). 1H NMR (CDCl3) δ: 7.46 (m, 4H), 7.31 (d, J=7.9 Hz, 2H), 7.15 (d, J=2.6 Hz, 1H), 6.85 (d, J=8.5 Hz, 2H), 6.78 (m, 2H), 4.30 (s, 2H), 3.81 (s, 3H), 1.68 (s, 6H).

Workup

  1. customThe title compound was prepared following procedure
  2. customThe crude (1.7 g) was purified by recrystallisation from MeOH/EtOAc

Sources & evidence

ORD record
ord-ac0bfbd6fe8c427dba40b5ba3df9f443
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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