Acetic Acid → 5-Iodo-6-methylpyridin-3-amine

HRID 1894904Notes

Reaction equation

HRID 1894904 reaction equation
[I:1][C:2]1[C:3]([CH3:11])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.C(O)(=O)C>C(O)C.CCOC(C)=O.O.C([O-])([O-])=O.[Na+].[Na+].[Fe]>[I:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[CH3:11]

Participants

8

Reactant 2

HCID 176Acetic AcidHCID 591983253-Iodo-2-methyl-5-nitropyridine

Product 1

HCID 591982915-Iodo-6-methylpyridin-3-amine

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-iodo-2-methyl-5-nitropyridine (125 mg, 0.4734 mmol) in ethanol (3 mL) was added acetic acid (0.50 mL, 8.8 mmol) and iron powder (140 mg, 2.6 mmol). The reaction was heated at 85° C. for 30 minutes and was diluted with EtOAc, water, and saturated Na2CO3. Then it was filtered and extracted with EtOAc and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and stripped in vacuo. 1H NMR (400 MHz, CDCl3): δ 7.96 (d, 1H), 7.44 (d, 1H), 3.57 (br s, 2H), 2.61 (s, 3H); MS (ES) (M+H)=235.

Workup

  1. filtrationThen it was filtered
  2. extractionextracted with EtOAc
  3. washthe organic extracts were washed with water, saturated NaCl
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-74a137b31200435abdca8cf2f79013da
Source dataset
uspto-grants-2013_08
Patent number
US08513270B2

Reaction notes

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