Hydrochloric Acid → Sodium Methoxide

HRID 1200029Notes

Reaction equation

HRID 1200029 reaction equation
[Na].[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)([OH:4])=[O:3].C[O-].[Na+:15].[CH2:16](N)[CH2:17][NH2:18].Cl>CO>[CH3:2][O-:3].[Na+:15].[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:18][CH2:17][CH2:16][N:12]=2)=[N:9][CH:10]=1)([OH:4])=[O:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 27611086-Cyanopyridine-3-carboxylic acidHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 2

HCID 10942334Sodium MethoxideHCID 19864556HCID 19864556, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methoxide is prepared by careful addition of sodium metal (13.6 g, 0.59 mol) to a flask containing methanol (500 ml) which is stirred. A solution of 5-carboxy-2-cyano-pyridine (36.0 g, 0.24 mol) in methanol (200 ml) is added to the sodium methoxide and the mixture heated for 2 h at 50°. After this time, freshly distilled ethylenediamine (28.8 g, 0.48 mol) and concentrated hydrochloric acid (64 ml) is added to the solution, which is then heated to 80° for 2.5 h. The reaction mixture is evaporated in vacuo to dryness. The residue is slurried in hot water (75 ml) for 15 min, filtered, washed with cold methanol (2×25 ml) and dried in vacuo at 60° to yield the title compound; m.p. 344°-345°.

Workup

  1. temperaturethe mixture heated for 2 h at 50°
  2. temperatureis then heated to 80° for 2.5 h
  3. customThe reaction mixture is evaporated in vacuo to dryness
  4. filtrationfiltered
  5. washwashed with cold methanol (2×25 ml)
  6. customdried in vacuo at 60°

Sources & evidence

ORD record
ord-d16f405fc2614b48949904e97768997b
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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