Water → 2-Chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

HRID 1039781Notes

Reaction equation

HRID 1039781 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([Cl:13])=[N:7][C:8](Cl)=[CH:9][C:10]=1[CH3:11])=[O:4].C([O-])([O-])=O.[K+].[K+].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]([Cl:13])=[N:7][C:8]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:9][C:10]=1[CH3:11])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 46911843Methyl 2,6-dichloro-4-methylnicotinate

Product 1

HCID 866643312-Chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylesterYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.2 g (23.7 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester, 3.94 g (28.5 mmol) K2CO3 and 2.06 ml (23.7 mmol) morpholine in DMF (48 ml) was heated to 60° C. for 16 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1) provided 1.95 g (7.2 mmol, 30%) 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-bff0af5adf0848cbbf883efc671b259b
Source dataset
uspto-grants-2013_10
Patent number
US08552200B2

Reaction notes

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