Water → HCID 21875489, compound

HRID 2378419Notes

Reaction equation

HRID 2378419 reaction equation
[NH2:1][C:2]1[C:9]([NH2:10])=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:14]([CH:16]=O)=O.O.[OH-].[NH4+]>C(O)(=O)C>[N+:11]([C:8]1[C:9]2[N:10]=[CH:16][CH:14]=[N:1][C:2]=2[C:3]([C:4]#[N:5])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7860GlyoxalHCID 14923Ammonium HydroxideHCID 218754572,3-Diamino-4-nitrobenzonitrile

Product 1

HCID 21875489HCID 21875489, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
22 °C

Procedure

2,3-Diamino-4-nitro-benzonitrile (0.050 g, 0.28 mmol, as prepared in WO-98/32439) was added to solution of glyoxal (40% in water, 0.032 mL, 0.28 mmol) in acetic acid (0.75 mL) and stirred at 22° C. for 3 h. The reaction was cooled to 0° C. and water (2.0 mL) was added and the pH was adjusted to 9.0 by addition of ammonium hydroxide which caused the product to precipitate. The mixture was then filtered and rinsed with cold water. Drying in vacuo gave 0.039 g (70%) of compound 468A as an orange solid. HPLC: 100% at 2.037 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 mincontaining 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customto precipitate
  3. filtrationThe mixture was then filtered
  4. washrinsed with cold water
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-0740753863824302913e445fb327796f
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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