HCID 178488850, compound → HCID 178488849, compound

HRID 496028Notes

Reaction equation

HRID 496028 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([N+:16]([O-])=O)[CH:15]=1>C(O)(=O)C.[Zn]>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([NH2:16])[CH:15]=1

Participants

4

Reactant 1

HCID 178488850HCID 178488850, compound

Product 1

HCID 178488849HCID 178488849, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

5-(3H-Imidazo[4,5-b]pyridin-2-yl)-2-methoxy-nitrobenzene (7.0 g, 26 mmol) was dissolved in 200 mL acetic acid, and zinc powder (35 g, 535 mmol) was added in portions. The zinc was added at such a rate as to keep the temperature of the reaction mixture under 40° C. After complete addition, the reaction mixture was stirred for 3 hours and filtered to give solid. The solids wee washed with water and acetic acid. The filtrate was rotary evaporated in vacuo, and the residue was partitioned between 1 M NaOH and chloroform. The aqueous layer was extracted several times with chloroform, and the combined organic layers were dried over magnesium sulfate, filtered, and rotary evaporated to give 0.71 g of 5-(3H-imidazo[4,5-b]pyridin-2-yl)-2-methoxy-phenylamine as a tan solid. 1H-NMR (CDCl3): δ 8.06 (dd, 1H), 7.66 (dd, 1H), 7.41 (s, 1H), 7.35 (dd, 1H), 6.91 (dd, 1H), 6.64 (d, 1H), 3.67 (s, 3H) ppm. Anal. (C13H12N4O1) C,H,N values were within 0.4% of the theoretical values.

Workup

  1. customunder 40° C
  2. additionAfter complete addition
  3. filtrationfiltered
  4. customto give solid
  5. washThe solids wee washed with water and acetic acid
  6. customThe filtrate was rotary evaporated in vacuo
  7. customthe residue was partitioned between 1 M NaOH and chloroform
  8. extractionThe aqueous layer was extracted several times with chloroform
  9. dry with materialthe combined organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. customrotary evaporated

Sources & evidence

ORD record
ord-9811e0f4c84543969f497591d6e0ce86
Source dataset
uspto-grants-2005_09
Patent number
US06943174B2

Reaction notes

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