Ammonium Hydroxide → HCID 178468551, compound

HRID 864900Notes

Reaction equation

HRID 864900 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][C:7]=1[NH2:8].[CH2:19](C(CC)(CC)C([O-])([O-])[O-])[CH3:20].[OH-].[NH4+]>C(O)(=O)C>[CH3:19][C:20]1[N:8]=[C:7]2[NH:6][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 21847042Diethyl 5,6-diamino-2,3-pyridinedicarboxylateHCID 21875354Triethylorthoaceate

Product 1

HCID 178468551HCID 178468551, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Diethyl 5,6-diamino-2,3-pyridinedicarboxylate (10.38 g, 0.041 mol) is stirred under an N2 atmosphere in 100 mL glacial acetic acid, to give a clear orange solution. Triethylorthoacetate (TEOA), (0.19 mol) is then added and the mixture is heated to reflux for 15 hours. The cooled solution is poured into ice water and neutralized with ammonium hydroxide. The solution is extracted with ethyl acetate, the combined organic layers washed with brine, dried over Na2SO4, filtered and concentrated to an oil. The oil is taken up in ethyl acetate and the desired product is precipitated by the addition of hexanes in two crops of beige solid, totalling 8.11 g (71.3%), having a melting point of 164°-165° C.

Workup

  1. customto give a clear orange solution
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 15 hours
  4. extractionThe solution is extracted with ethyl acetate
  5. washthe combined organic layers washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customthe desired product is precipitated by the addition of hexanes in two crops of beige solid, totalling 8.11 g (71.3%)

Sources & evidence

ORD record
ord-846dc6fedd0f47a6b7345e4c455968fe
Source dataset
uspto-grants-1996_10
Patent number
US05565411

Reaction notes

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