Formic Acid → HCID 67251974, compound

HRID 2042047Notes

Reaction equation

HRID 2042047 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.C(O)=O>CO.[Pd]>[CH3:1][C:2]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 67253353HCID 67253353, compound

Product 1

HCID 67251974HCID 67251974, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(2-methyl-5-nitrophenoxy)pyridine (80 mg, 0.35 mmol) and 10% Pd/C (50% wet, 165 mg, 0.08 mmol) in methanol (4 mL) was treated with formic acid (89%, 1 mL, 35 mmol) and the resultant solution was stirred at RT. After 1 h, the reaction mixture was filtered through Celite®, and the filter cake was washed with methanol. The filtrates were concentrated in vacuo, diluted with 40 mL of a pH 12 aqueous solution and extracted with ethyl acetate (3×25 mL). The extracts were dried (Na2SO4) and concentrated in vacuo to provide 4-methyl-3-(pyridin-3-yloxy)benzenamine (58 mg, 83% yield). 1H NMR (400 MHz, CDCl3) δ 8.36 (m, 2H), 8.32 (dd, J=4.6, 1.4 Hz, 1H), 7.26-7.18 (m, 3H), 7.05 (d, J=8.0 Hz, 1H), 6.49 (dd, J=8.8, 2.4 Hz, 1H), 6.29 (d, J=2.4 Hz, 1H), 2.11 (s, 3H); MS (ESI) m/z: 201.0 (M+H+).

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. washthe filter cake was washed with methanol
  3. concentrationThe filtrates were concentrated in vacuo
  4. additiondiluted with 40 mL of a pH 12 aqueous solution
  5. extractionextracted with ethyl acetate (3×25 mL)
  6. dry with materialThe extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a42cb1f6a23848349c7314df448be604
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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