Benzenamine, N,N-diethyl-4-nitroso- → HCID 13007347, compound

HRID 982585Notes

Reaction equation

HRID 982585 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:9]=[CH:8][C:7]([N:10]=O)=[CH:6][CH:5]=1)[CH3:2].[C:14]1([C:20]2[CH:24]=[C:23]([NH2:25])[N:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:9]=[C:8]2[C:7]([N:10]=[C:24]3[C:20]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)=[N:21][N:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[C:23]3=[N:25]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 67115Benzenamine, N,N-diethyl-4-nitroso-HCID 122881361-pyridyl-3-phenyl-5-aminopyrazole

Product 1

HCID 13007347HCID 13007347, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.78 g N,N-diethyl-p-nitrosoaniline and 2.67 g 3-phenyl-1-(2-pyridyl)-5-aminopyrazole were refluxed for 2 hrs in acetic acid. The mixture was concentrated to half volume. Water was added to get a precipitate, then filtered. The solid was purified by chromatograph column on silica gel. After removing the solvent, 1.3 g pure 7-diethylamino-3-phenyl-1-(2-pyridyl)-1H-pyrazolo[3,4-b]quinoxaline (DEPPPQ) was obtained as brown-red solid.

Workup

  1. concentrationThe mixture was concentrated to half volume
  2. additionWater was added
  3. customto get a precipitate
  4. filtrationfiltered
  5. customThe solid was purified by chromatograph column on silica gel
  6. customAfter removing the solvent

Sources & evidence

ORD record
ord-9ae09d0d5ca34207b203d51523b20b61
Source dataset
uspto-grants-2005_03
Patent number
US06861162B2

Reaction notes

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