Methoxyacetic Acid → HCID 19012215, compound

HRID 466697Notes

Reaction equation

HRID 466697 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][O:11][CH2:12][C:13](O)=O.[NH4+].[OH-]>CO>[CH3:10][O:11][CH2:12][C:13]1[NH:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[CH:5][C:6]=2[CH3:9]

Participants

5

Reactant 3

HCID 12251Methoxyacetic AcidHCID 14923Ammonium HydroxideHCID 3174954-Methylpyridine-2,3-diamine

Product 1

HCID 19012215HCID 19012215, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 2,3-diamino-4-picoline (0.1 g, 0.81 mmol) and methoxyacetic acid (0.16 ml, 2 mmol) was heated in a sealed tube at 165° C. for 24 hours. The reaction was cooled and neutralized with NH4OH. The crude material was dissolved in methanol (2 ml) and silica-gel (10 g) was added. The dried silica-gel was then loaded on a silica-gel flash-column and eluted initially with EtOAc and then with 2% methanol in EtOAc. The pure desired compound was obtained as a cream colored solid (0.067 g, 47%).

Workup

  1. temperatureThe reaction was cooled
  2. additionsilica-gel (10 g) was added
  3. washeluted initially with EtOAc

Sources & evidence

ORD record
ord-f713067166c740c182ef6ea739ddcdcc
Source dataset
uspto-grants-1992_10
Patent number
US05157026

Reaction notes

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