Sodium Hydroxide → 6-Chloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinic acid

HRID 2044079Notes

Reaction equation

HRID 2044079 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[CH:16][CH:15]=2)[C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[OH-].[Na+]>CCO.C1COCC1>[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[CH:16][CH:15]=2)[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57489629Ethyl 6-chloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinate

Product 1

HCID 574896306-Chloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinic acidYield 86.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 6-chloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinate (300 mg, 0.770 mmol) in EtOH (6 mL) and THF (6.00 mL) was treated with 30% aqueous sodium hydroxide (2 mL, 26.0 mmol) and stirred at rt for 3 hrs. Remove most of the solvent on rotary evaporator and acidified with 1N HCl (no precipitate formed) and extracted into CH2Cl2 several times and the combined extracts were concentrated to give 240 mg of 6-chloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinic acid. LCMS: (M+H)+=362.02, 363.93 (Cl pattern).

Workup

  1. customRemove most of the solvent on rotary evaporator
  2. customformed) and
  3. extractionextracted into CH2Cl2 several times
  4. concentrationthe combined extracts were concentrated

Sources & evidence

ORD record
ord-99aae3667d194a8fbb6f62bd21b1db97
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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