Hydrochloric Acid → HCID 20475365, compound

HRID 2295395Notes

Reaction equation

HRID 2295395 reaction equation
[CH3:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:4][C:5]([CH2:8][O:9]C(=O)C)=[CH:6][CH:7]=1.Cl>[OH-].[Na+].C(O)C>[CH3:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:4][C:5]([CH2:8][OH:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20475368HCID 20475368, compound

Product 1

HCID 20475365HCID 20475365, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.4 g (5.8 mmols) of 3-methyl-6-acetoxymethyl-2,2'-bipyridine are boiled under reflux for 30 minutes in a mixture of 20 ml of 10% sodium hydroxide solution and 15 ml of ethanol. After cooling, the mixture is acidified with hydrochloric acid and washed with twice 20 ml of ethyl acetate. The aqueous phase is rendered alkaline with potassium carbonate, and the reaction product is extracted with 40 ml of ethyl acetate. After drying over sodium sulfate and concentration in vacuo, the 3-methyl-6-hydroxymethyl-2,2'-bipyridine is crystallised from diethyl ether. Yield: 0.99 g (85% of theory); melting point 51°-53° C. UV absorption (in chloroform): λmax =281 nm (ε=9400).

Workup

  1. temperatureAfter cooling
  2. washwashed with twice 20 ml of ethyl acetate
  3. extractionthe reaction product is extracted with 40 ml of ethyl acetate
  4. dry with materialAfter drying over sodium sulfate and concentration in vacuo
  5. customthe 3-methyl-6-hydroxymethyl-2,2'-bipyridine is crystallised from diethyl ether
  6. customUV absorption (in chloroform)

Sources & evidence

ORD record
ord-154de8da489945edbee2068994b2c872
Source dataset
uspto-grants-1984_01
Patent number
US04424359

Reaction notes

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