Hydrochloric Acid → HCID 13339619, compound

HRID 1632123Notes

Reaction equation

HRID 1632123 reaction equation
COC(=O)[C:4]1[CH:9]=[C:8](OC)[N:7]=[C:6](Cl)[CH:5]=1.[CH3:14][Mg]Br.[CH2:17]([O:19][CH2:20][CH3:21])C.[ClH:22].[OH2:23]>C1C=CC=CC=1>[Cl:22][C:8]1[CH:9]=[C:4]([C:5]([CH3:6])([CH3:14])[OH:23])[CH:21]=[C:20]([O:19][CH3:17])[N:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 13339618Methyl 2-chloro-6-methoxyisonicotinateHCID 178418573HCID 178418573, compound

Product 1

HCID 13339619HCID 13339619, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 155.7 g (0.772 mole) of methyl-2-chloro-6-methoxyisonicotinate dissolved in 2.0 liter of benzene was added a solution of 563 ml of 3.0M methyl magnesium bromide in diethyl ether (1.69 moles) dropwise over one hour. The slurry was heated at reflux for 1.5 hours and cooled to 10° C. in an ice bath. To the cold slurry was added dropwise a solution of 300 ml of concentrated hydrochloric acid dissolved in 1200 ml of water. The mixture was allowed to warm to room temperature and the organic layer separated and washed with water, 1N sodium hydroxide and dried (Na2SO4). Removal of solvent in vacuo afforded 142.3 g (91.4% yield) of desired 2-chloro-6-methoxy-α,α-dimethyl-4-pyridinemethanol.

Workup

  1. temperatureThe slurry was heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureto warm to room temperature
  4. customthe organic layer separated
  5. washwashed with water, 1N sodium hydroxide
  6. dry with materialdried (Na2SO4)
  7. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-947407fd8b954fb384b238e55a8ac4fe
Source dataset
uspto-grants-1984_10
Patent number
US04474602

Reaction notes

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