Hydrochloric Acid → 6-(Morpholine-4-carbonyl)nicotinic acid

HRID 1385884Notes

Reaction equation

HRID 1385884 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]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 100857186-(Morpholine-4-carbonyl)nicotinic acid, t-butyl ester

Product 1

HCID 101055146-(Morpholine-4-carbonyl)nicotinic acidYield 68.5%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

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.

Workup

  1. customthe solvent was removed in vacuo
  2. customto give a pale yellow solid
  3. customRecrystallization (acetone)

Sources & evidence

ORD record
ord-1276d27350fe4f7ba80f6edbccfdd9ba
Source dataset
uspto-grants-2001_07
Patent number
US06265381B1

Reaction notes

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