2-Thiophenecarboxaldehyde → 3-[(Thiophen-2-ylmethyl)-amino]-phthalic acid dimethyl ester
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH3:8][O:9][C:10](=[O:27])[C:11]1[C:12](=[C:17]([NH:21]CCCCC)[CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH3:16])=[O:14]>>[CH3:8][O:9][C:10](=[O:27])[C:11]1[C:12](=[C:17]([NH:21][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH3:16])=[O:14]Participants
3
Procedure
2-Thiophenecarboxaldehyde (1.12 g, 10 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. The residue (oil) was purified by preparative HPLC (Symmetry C18, isocratic, 45% acetonitrile/water) to give 0.88 g (58%) of yellow oil: 1H NMR (CDCl3) δ 7.38–7.15 (m, 3H), 7.00–6.93 (m, 2H), 6.87–6.82 (m, 2H), 4.58 (d, J=5.3 Hz, 2H), 3.86 (s, 3H), 3.83 (s, 3H).
Workup
- customThe residue (oil) was purified by preparative HPLC (Symmetry C18, isocratic, 45% acetonitrile/water)