Nitric Acid → 2-nitro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol

HRID 491689Notes

Reaction equation

HRID 491689 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[C:4]2[CH:3]=[CH:2]1.[N+:18]([O-])([OH:20])=[O:19]>CC(O)=O>[N+:18]([C:15]1[CH:16]=[C:11]([O:10][C:9]2[CH:8]=[CH:7][N:6]=[C:5]3[NH:1][CH:2]=[CH:3][C:4]=23)[CH:12]=[CH:13][C:14]=1[OH:17])([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 576785554-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)phenol

Product 1

HCID 576784942-nitro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)phenol (Step b, 5.6 g, 24.8 mmol, 1.0 eq.) was dissolved into AcOH (100 ml) and HNO3 (70%, 2.4 mL, 26.7, 1.1 eq.) was added dropwise. The reaction was stirred for 1 h at RT. The acids were removed by evaporation and the residue was taken up in NaHCO3 (aq., saturated, 100 mL) and CH2Cl2 (200 mL). Separated the layers and washed the organic layers with NaHCO3 (aq., saturated, 50 mL) and brine (50 mL). Back extracted aqueous layers with CH2Cl2 (100 ml) and dried the combined organic layers over MgSO4, filtered and concentrated. Further purification by column chromatography (0-100% EtOAc/Hexane) yielded 2-nitro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol.

Workup

  1. additionwas added dropwise
  2. customThe acids were removed by evaporation
  3. customSeparated the layers
  4. washwashed the organic layers with NaHCO3 (aq., saturated, 50 mL) and brine (50 mL)
  5. extractionBack extracted aqueous layers with CH2Cl2 (100 ml)
  6. dry with materialdried the combined organic layers over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFurther purification by column chromatography (0-100% EtOAc/Hexane)

Sources & evidence

ORD record
ord-29e02bd3cbe14f4b9200bd7b588ef6bc
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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