Sodium Hydroxide → 5-Methoxy-4-methylpyridin-3-amine

HRID 2374153Notes

Reaction equation

HRID 2374153 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:23])=[C:5]([N:9]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=[N:7][CH:8]=1.Cl.C1COCC1.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[C:4]([CH3:23])=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 18422008HCl tetrahydrofuranHCID 86760778HCID 86760778, compound

Product 1

HCID 127063385-Methoxy-4-methylpyridin-3-amine

Conditions

Temperature
55 °C

Procedure

To 5-methoxy-4-methyl-N-(diphenylmethylene)pyridine-3-amine (0.7g) in a single neck round bottle flask, was added 14 ml of 1N HCl/THF (1:1) and the resulting mixture heated at 55° C. for 1 h. The reaction was basified with 1N NaOH to pH9, extracted with DCM, dried over Na2SO4, and concentrated to dryness under vacuum affording 5-methoxy-4-methyl-pyridin-3-ylamine. MS (ESI+) for m/z 139 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-a79acb7198a841b099dd534e7999f3d7
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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