Hydrazinecarboxaldehyde → HCID 18349248, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:39]([NH:41][NH2:42])=O.P(Cl)(Cl)(Cl)=O>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[CH2:12][C:13]2[O:15][CH:39]=[N:41][N:42]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]Participants
Procedure
2-[1-(3,4-Dimethoxyphenyl)-2-(1,3,4-oxadiazol-2-yl)ethyl]isoindoline-1,3-dione was prepared by the procedure of Example 8 from 3-(3,4-dimethoxyphenyl)-3-(1,3-dioxoisoindolin-2-yl)propanoic acid (2.0 g, 3.6 mmol), carbonyidiimidazole (1.0 g, 6.2 mmol), formic hydrazide (0.41 g, 6.8 mmol), and phosphorus oxychloride (1.3 mL, 14 mmol) in acetonitrile (20 mL). The product was obtained as a white solid (730 mg, 34% yield): mp, 83.0-85.0° C.; 1H NMR (CDCl3) δ 3.82 (dd, J=6.0, 16.0 Hz, 1H, CHH), 3.85 (s, 3H, CH3), 3.90 (s, 3H, CH3), 4.39 (dd, J=10.3, 15.7 Hz, 1H, CHH), 5.84 (dd, J=6.0, 10.3 Hz, 1H, NCH), 6.81-6.85 (m, 1H, Ar), 7.16-7.19 (m, 2H, Ar), 7.68-7.73 (m, 2H, Ar), 7.77-7.83 (m, 2H, Ar), 8.30 (s, 1H, CH); 13C NMR (CDCl3) δ 27.66, 51.76, 55.79, 55.89, 111.00, 111.07, 120.29, 123.3,8, 130.16, 131.55, 134.07, 149.03, 149.11, 152.96, 163.90, 167.86; Anal Calcd for C20H17N3O6+0.3 Et2O: C, 63.22; H, 5.20; N, 10.32. Found: C, 63.40; H, 5.02; N, 10.46. (1H NMR showed that the sample contained 30% of ether).
Sources & evidence
- ORD record
- ord-a924e2e72f6547fa830b3f707fa845ab
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326388B1
Reaction notes
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