Sodium hydroxide ethanol → 5-Trifluoromethyl-6-(morpholin-4-yl)-nicotinic acid

HRID 1820987Notes

Reaction equation

HRID 1820987 reaction equation
[N:1]1([C:7]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11]C(C#N)=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-:19].[Na+].[CH3:21][CH2:22][OH:23]>>[F:14][C:13]([F:16])([F:15])[C:12]1[C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[N:8][CH:9]=[C:21]([CH:11]=1)[C:22]([OH:19])=[O:23]

Participants

3

Reactant 2

HCID 23692425Sodium hydroxide ethanolHCID 688505062-(Morpholin-4-yl)-3-trifluoromethyl-5-cyanopyridine

Product 1

HCID 688502085-Trifluoromethyl-6-(morpholin-4-yl)-nicotinic acid

Procedure

A solution of 249 mg (0.97 mmol) of 2-(morpholin-4-yl)-3-trifluoromethyl-5-cyanopyridine (from Step D) in 5 mL 1:1 v/v 5 N NaOH/EtOH was heated at reflux for 1 h. The mixture was cooled and partitioned between 20 mL of ether and 20 mL of water. The aqueous layer was separated and adjusted to pH=4 with conc. HCl. The precipitated solid was filtered, rinsed with water and dried to afford 138 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 3.52 (app t, J=5.0, 4H), 3.78 (app t, J=5.0, 4H), 8.40 (d, J=2.0, 1H), 8.90 (d, J=2.0, 1H); ESI-MS (m/z) 277.3; HPLC A: 2.71 min.

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe mixture was cooled
  3. custompartitioned between 20 mL of ether and 20 mL of water
  4. customThe aqueous layer was separated
  5. filtrationThe precipitated solid was filtered
  6. washrinsed with water
  7. customdried

Sources & evidence

ORD record
ord-6f0230fda58e4675844e4a35e371b451
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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