Sodium Hydroxide → 2-(((5-Aminopyridin-2-yl)methyl)(methyl)amino)ethanol

HRID 55884Notes

Reaction equation

HRID 55884 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][OH:19])=[N:13][CH:14]=1)C1C=CC=CC=1.[OH-].[Na+]>S(=O)(=O)(O)O>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][OH:19])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71238254HCID 71238254, compound

Product 1

HCID 866761742-(((5-Aminopyridin-2-yl)methyl)(methyl)amino)ethanolYield 50.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 40 (400 mg, 1.1 mmol) in conc. sulfuric acid (1.3 mL) was heated at 50° C. for 3 h. The reaction mixture was cooled to 0° C., basified with 2N NaOH solution (15 mL) to pH ˜9 and extracted with 10% MeOH/CHCl3 (2×100 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and evaporated to obtain the desired amine (100 mg, 50%) as a brown liquid. Rf: 0.4 (10% MeOH/CHCl3, alumina plate); (m/z): 182 [MH]+; 1H NMR (400 MHz, DMSO-d6) δ 7.82 (1H, d, J=2.4 Hz), 7.05 (1H, d, J=8.4 Hz), 6.87 (1H, dd, J=2.8, 8.0 Hz), 5.15 (2H, s), 4.38 (1H, br s), 3.47-3.43 (4H, m), 2.42 (2H, t, J=6.4 Hz), 2.15 (3H, S).

Workup

  1. extractionextracted with 10% MeOH/CHCl3 (2×100 mL)
  2. washThe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3cd9a7a88b074a808ab2b44d332d5257
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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