Hydrochloric Acid → 6-(Morpholine-4-carbonyl)nicotinic acid
Reaction equation
[N:1]1([C:7]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15]C(C)(C)C)=[O:14])=[CH:11][N:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl>C[N+]([O-])=O>[N:1]1([C:7]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a solution of the compound of Example 11 (b) (0.606 g, 2.07 mmol) in CH3NO2 (5 mL) was bubbled HCl(g) for 20 min. After standing for 20 min, the solvent was removed in vacuo to give a pale yellow solid. Recrystallization (acetone) gave 0.335 g (68%) of the title compound as a white solid. Mp: 181-183° C. 1H NMR (CD3OD): δ9.26 (d, J=1.1 Hz, 1H), 8.78 (dd, J=8.1 Hz, 1H), 3.80 (s, 4H), 3.67 (m, 2H), 3.51 (m, 2H). IR (KBr): 2928, 2872, 1717, 1601, 1285, 1262, 1111 cm−1. MS (DCI/CH4): m/z (rel intensity) 277 (M +C3H7+), 265 (M+C2H5+), 238, 237 (MH+, 100). Anal. (C11H12N2O4): C, H, N.