Nitric Acid → Methyl-3-nitro-thieno[2,3-c]pyridine

HRID 254438Notes

Reaction equation

HRID 254438 reaction equation
[CH3:1][C:2]1[S:10][C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.[N+:11]([O-])([OH:13])=[O:12].[OH-].[Na+].O.C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[CH3:1][C:2]1[S:10][C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 121308462-Methylthieno[2,3-c]pyridineHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 66859381Methyl-3-nitro-thieno[2,3-c]pyridineYield 46%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-Methyl-thieno[2,3-c]pyridine (5.51 g, 36.9 mmol) was dissolved in concentrated H2SO4 (20 mL) at 0° C. Concentrated HNO3 (11.6 mL) was added dropwise over 15 min, followed by warming to RT. Stirred for 18 h at RT. The solution was poured over ice and adjusted pH to 7 with 50% NaOH/H2O and sat NaHCO3 solution. The solution was extracted with portions of CH2Cl2 (3×100 mL), dried (MgSO4) and condensed to yield the title compound as a bright yellow solid (3.27 g, 46%).

Workup

  1. extractionThe solution was extracted with portions of CH2Cl2 (3×100 mL)
  2. customdried
  3. custom(MgSO4) and condensed

Sources & evidence

ORD record
ord-fbf3f1146ede44cd942f788d9f16ba2e
Source dataset
uspto-grants-2011_01
Patent number
US07875627B2

Reaction notes

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