Nitric Acid → HCID 86760861, compound

HRID 491679Notes

Reaction equation

HRID 491679 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:27]([O-])([OH:29])=[O:28].C([O-])(O)=O.[Na+]>CC(O)=O>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 516892Sodium BicarbonateHCID 86760862HCID 86760862, compound

Product 1

HCID 86760861HCID 86760861, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(4-hydroxy-phenoxy)-pyridine-2-carboxylic acid (4-pyrrolidin-1-yl-butyl)-amide (Step C, 2.0 g, 5.6 mmol) in HOAc (32 mL) at RT was added 70% HNO3 (0.56 g, 6.2 mmol). The reaction was stirred at RT for 18 h. An additional amount of 70% HNO3 (0.56 g, 6.2 mmol) was added dropwise over 10 min, and the reaction was stirred for 2 h, after which it was slowly added to saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel chromatography to yield the title compound. MS (MH+)=401.2; Calc'd 400.44 for C20H24N4O5.

Workup

  1. stirringthe reaction was stirred for 2 h
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3c14fbf5d0094065bb468a51002887fc
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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