Glyoxal → HCID 21875489, compound

HRID 723677Notes

Reaction equation

HRID 723677 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.[OH-].[NH4+]>O.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 3

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

Product 1

HCID 21875489HCID 21875489, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2,3-Diamino-4-nitro-benzonitrile (0.050 g, 0.28 mmol, as prepared in WO98/32439) was added to solution of glyoxal (40% in water, 0.032 m]L, 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 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. customto precipitate
  2. filtrationThe mixture was then filtered
  3. washrinsed with cold water
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-002d54f67d4544759bb7221be4e2ee6e
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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