2-Isopropylaniline → 2-[(2-Isopropyl)phenylamino]-isophthalic acid
Reaktionsgleichung
I[C:2]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:14]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19])([CH3:16])[CH3:15]>>[CH:14]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([CH3:16])[CH3:15]Komponenten
3
Versuchsvorschrift
Similar reaction of 2-iodoisophthalic acid and 2-isopropylaniline gave 2-[(2-isopropyl)phenylamino]-isophthalic acid (38%), mp (EtOAc/petroleum ether) 217-219° C. 1H NMR [(CD3)2SO] δ 1.25 (d, J=6.8 Hz, 6 H, 2×CH3), 3.22-3.29 (m, 1 H, CH), 6.81 (dd, J=7.4, 1.8 Hz, 1 H, H-3' or H-6'), 6.93 (t, J=7.7 Hz, 1 H, H-2), 6.92-7.02 (m, 2 H, H-4' and H-5'), 7.26 (dd, J=7.1, 2.2 Hz, 1 H, H-6' or H-3'), 7.90 (d, J=7.7 Hz, 2 H, H-4 and H-6), 9.69 (s, 1 H, NH), 12.93 (br s, 2 H, 2×COOH). Anal. (C17H17NO4) C, H, N.
Quellen und Nachweise
- ORD-Eintrag
- ord-016d126452e54a86a3bc93467d7a1ded
- Quelldatensatz
- uspto-grants-2000_09