1,2-Naphthalenedicarboxylic anhydride → 3-(1,3-Dioxobenzo[e]isoindolin-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanenitrile

HRID 1295885

Reaction equation

HRID 1295885 reaction equation
[C:1]1(=[O:15])[C:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]=2[C:3](=[O:14])O1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[NH2:16][CH:17]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=1)[CH2:18][C:19]#[N:20]>C(O)(=O)C>[O:15]=[C:1]1[C:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH:12]=[CH:13][C:4]=2[C:3](=[O:14])[N:16]1[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=1)[CH2:18][C:19]#[N:20]

Participants

4

Reactant 2

HCID 214371,2-Naphthalenedicarboxylic anhydrideHCID 221771543-Amino-3-(3-ethoxy-4-methoxyphenyl)propanenitrile

Product 1

HCID 115168893-(1,3-Dioxobenzo[e]isoindolin-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanenitrileYield 48.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of naphtho[1,2-c]furan-1,3-dione (440 mg, 2.2 mmol) and 3-amino-3-(3-ethoxy-4-methoxy-phenyl)-propionitrile (490 mg, 2.2. mmol) in acetic acid (10 mL) was heated to reflux overnight. The solvent was removed in vacuo to give a solid, which was purified with chromatography (Silica Gel, CH2Cl2) to give 3-(1,3-dioxobenzo[e]isoindolin-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanenitrile as a yellow solid (430 mg, 48% yield): mp 163.0-165.0° C.; 1H NMR (CDCl3) δ 1.46 (t, J=7 Hz, 3H, CH3), 3.34 (dd, J=7, 17 Hz, 1H, CHH), 3.80-3.92 (m, 1H, CHH), 3.84 (s, 3H, CH3), 4.10 (q, J=7 Hz, 2H, CH2), 5.67 (dd, J=7, 10.1 Hz, 1H, NCH), 6.82-6.86 (m, 1H, Ar), 7.11-7.13 (m, 2H, Ar), 7.61-7.74 (m, 2H, Ar), 7.81 (d, J=8 Hz, 1H, Ar), 7.92 (d, J=7.9 Hz, 1H, Ar), 8.14 (d, J=8.3 Hz, 1H, Ar), 8.87 (d, J=8 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.66, 21.22, 50.97, 55.91, 64.48, 111.43, 112.19, 117.00, 118.46, 120.03, 124.79, 126.79, 127.96, 128.73, 128.94, 129.24, 129.66, 130.78, 135.37, 136.68, 148.56, 149.72, 168.37, 168.92. Analy. calculated for C24H20N2O4: C, 71.99; H, 5.03; N, 7.00. Found: C, 71.81; H, 5.04; N, 7.00.

Workup

  1. temperatureto reflux overnight
  2. customThe solvent was removed in vacuo
  3. customto give a solid, which
  4. customwas purified with chromatography (Silica Gel, CH2Cl2)

Sources & evidence

ORD record
ord-0a6be191185e4c00a65d215a72aaa54a
Source dataset
uspto-grants-2007_07
Patent number
US07244759B2

Linked notes

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