Acetic Anhydride → HCID 67273765, compound

HRID 1696778Notes

Reaction equation

HRID 1696778 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH2:12])[N:11]=1)[C:5]([NH:7][OH:8])=[NH:6].[C:13](OC(=O)C)(=O)[CH3:14]>>[CH3:13][C:14]1[O:8][N:7]=[C:5]([C:4]2[CH:3]=[C:2]([NH2:1])[N:11]=[C:10]([NH2:12])[CH:9]=2)[N:6]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178513376HCID 178513376, compound

Product 1

HCID 67273765HCID 67273765, compound

Procedure

A solution of 0.134 g 2,6-diamino-N-hydroxy-isonicotinamidine (Example 108a) in 2.00 ml acetic acid anhydride was heated to reflux for 4 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was dried over magnesium sulfate dihydrate and evaporated. The residue was taken up in 2 ml 2N hydrochloric acid and heated to reflux for 1.5 h. The mixture neutralized by addition of 3 ml 1N sodium hydroxide and partitioned between water and ethyl acetate. The phases were separated and the organic phase was washed with brine and evaporated to yield 0.071 g of the title compound as brown solid.

Workup

  1. temperatureto reflux for 4 h
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over magnesium sulfate dihydrate
  5. customevaporated
  6. temperatureheated
  7. temperatureto reflux for 1.5 h
  8. additionThe mixture neutralized by addition of 3 ml 1N sodium hydroxide
  9. custompartitioned between water and ethyl acetate
  10. customThe phases were separated
  11. washthe organic phase was washed with brine
  12. customevaporated

Sources & evidence

ORD record
ord-1dccca5c564d44d988291e9670be2858
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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