2-Chloro-4-nitropyridine 1-oxide → HCID 178478252, compound

HRID 1387159Notes

Reaction equation

HRID 1387159 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[Cl:9][C:10]1[CH:15]=[C:14]([N+]([O-])=O)[CH:13]=[CH:12][N+:11]=1[O-].C(=O)(O)[O-].[K+]>CC(O)C>[NH:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:14]2[CH:13]=[CH:12][N:11]=[C:10]([Cl:9])[CH:15]=2)[N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 844332-Chloro-4-nitropyridine 1-oxideHCID 516893Potassium BicarbonateHCID 178419017HCID 178419017, compound

Product 1

HCID 178478252HCID 178478252, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

38 mg (0.34 mmol) of histamine and 55 mg (0.31 mmol) of 2-chloro-4-nitropyridine N-oxide in 15 ml of 2-propanol are stirred with potassium bicarbonate at 21° C. for 3 days. The mixture is then filtered and evaporated. The resulting solid residue is chromatographed on a column of silica gel, using a chloroform/methanol (10/1) mixture. The pure fractions are evaporated under reduced pressure to give the title compound which, after crystallization from a 2-propanol/ether (1/1) mixture, melts at 164°-165° C.

Workup

  1. filtrationThe mixture is then filtered
  2. customevaporated
  3. customThe resulting solid residue is chromatographed on a column of silica gel
  4. customThe pure fractions are evaporated under reduced pressure

Sources & evidence

ORD record
ord-b710038757814238a6e568aeaa60e608
Source dataset
uspto-grants-2001_07
Patent number
USRE037303E1

Reaction notes

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