Formamide → HCID 12840849, compound

HRID 2051617Notes

Reaction equation

HRID 2051617 reaction equation
[CH:1]([NH2:3])=O.[CH3:4][O:5][C:6]([C:8]1[CH:21]=[C:20]([NH2:22])[C:19]2[C:18](=[O:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:24])[C:10]=2[C:9]=1[NH2:25])=[O:7].[C-]#N.[Na+].[Cl-].[NH4+].[OH-].[Na+]>O.CO>[CH3:4][O:5][C:6]([C:8]1[C:21]([C:1]#[N:3])=[C:20]([NH2:22])[C:19]2[C:18](=[O:23])[C:17]3[C:12]([C:11](=[O:24])[C:10]=2[C:9]=1[NH2:25])=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:7]

Participants

8

Reactant 5

HCID 713FormamideHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 12840848HCID 12840848, compound

Product 1

HCID 12840849HCID 12840849, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 500 parts of formamide and 80 parts of methanol is prepared and 80 parts of 1,4-diamino-anthraquinone-2-carboxylic acid methyl ester and 60 parts of sodium cyanide are introduced, whilst stirring. The mixture is heated to 50° C. and a gentle stream of air is passed through it, whilst stirring. Stirring is continued until a thin layer chromatogram indicates that no starting material is left; this is generally the case after 5 hours. After cooling, the reaction mixture is added to 1,000 parts of water and 500 parts of ice, whilst stirring, and 200 parts of ammonium chloride are added to buffer the sodium hydroxide formed. The suspension is subsequently stirred whilst passing air through it, and the product is filtered off, washed neutral with warm water and rinsed with a little methanol. After drying, 81.5 parts of 1,4-diamino-2-cyano-anthraquinone-3-carboxylic acid methyl ester are obtained; melting point 914°-198° C.

Workup

  1. customis prepared
  2. stirringwhilst stirring
  3. stirringStirring
  4. waitis left
  5. customafter 5 hours
  6. temperatureAfter cooling
  7. stirringwhilst stirring
  8. customformed
  9. stirringThe suspension is subsequently stirred
  10. filtrationthe product is filtered off
  11. washwashed neutral with warm water
  12. washrinsed with a little methanol
  13. customAfter drying

Sources & evidence

ORD record
ord-5e80c0c696a344d79c5944f9321b7ce7
Source dataset
uspto-grants-1980_01
Patent number
US04181668

Reaction notes

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