Sodium Nitrite → 6-(4-Benzyloxyphenoxy)pyridin-3-ol

HRID 1260542Notes

Reaction equation

HRID 1260542 reaction equation
N([O-])=[O:2].[Na+].[CH2:5]([O:12][C:13]1[CH:26]=[CH:25][C:16]([O:17][C:18]2[N:23]=[CH:22][C:21](N)=[CH:20][CH:19]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>S(=O)(=O)(O)O.C(O)(=O)C>[CH2:5]([O:12][C:13]1[CH:26]=[CH:25][C:16]([O:17][C:18]2[N:23]=[CH:22][C:21]([OH:2])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 288183036-(4-Benzyloxyphenoxy)pyridin-3-ylamine

Product 1

HCID 670715476-(4-Benzyloxyphenoxy)pyridin-3-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

Sodium nitrite (1.84 g, 26.7 mmol) was dissolved in 32 ml of concentrated sulfuric acid at 0° C. Then, 6-(4-benzyloxyphenoxy)pyridin-3-ylamine (7.1 g, 24.29 mmol) in 75 ml of acetic acid were slowly added dropwise. After 1 h the ice bath was removed and stirring was continued for an hour. The reaction mixture was added dropwise to 250 ml of boiling water, and the mixture was stirred for 1 hour and after cooling extracted with ethyl acetate. The precipitated solid was filtered off and the filtrate was concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 269 mg (4%), M+H+: 294.10.

Workup

  1. customAfter 1 h the ice bath was removed
  2. waitwas continued for an hour
  3. additionThe reaction mixture was added dropwise to 250 ml of boiling water
  4. stirringthe mixture was stirred for 1 hour
  5. temperatureafter cooling
  6. extractionextracted with ethyl acetate
  7. filtrationThe precipitated solid was filtered off
  8. concentrationthe filtrate was concentrated
  9. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-fb89e7cafb5d48c58684e6915b98c415
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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