Hydrochloric Acid → HCID 10516434, compound

HRID 1756635Notes

Reaction equation

HRID 1756635 reaction equation
COC[O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[N:10][CH:11]=1.Cl>CO>[OH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10829341HCID 10829341, compound

Product 1

HCID 10516434HCID 10516434, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-methoxymethoxymethyl-2-[2-(4-nitrophenoxy)ethyl]pyridine (14.5 g), 2N hydrochloric acid (50 ml) and methanol (50 ml) was stirred under reflux for 2 hours. The reaction mixture was concentrated and the residue was neutralized with saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to obtain 5-hydroxymethyl-2-[2-(4-nitrophenoxy)ethyl]pyridine (9.7 g, yield: 88%). This compound was recrystallized from ethyl acetate to obtain colorless prisms, m.p. 144°-145° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd1b7e8c89e64218800bb7e56d6b325d
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

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