Methanol → HCID 69042848, compound

HRID 877958Notes

Reaction equation

HRID 877958 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])([O-])=O.CO>C(O)(=O)C.CCOC(C)=O.[Zn]>[C:11]1([CH3:16])[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[NH2:1]

Participants

6

Reactant 2

HCID 887MethanolHCID 69043784HCID 69043784, compound

Product 1

HCID 69042848HCID 69042848, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

Zinc dust (3.0 g, 46 mmol) was added to 3-nitro-4-o-tolyl-pyridine (1.35 g, 6.3 mmol) in acetic acid (32 mL). The reaction mixture was heated to 70° C. for 90 min. After cooling to room temperature, solids were removed from the reaction mixture by filtration. Evaporation of volatiles in vacuo gave a solid that was triturated with toluene. Removal of solids by filtration followed by evaporation of volatiles in vacuo gave a heavy oil. The product 4-o-tolyl-pyridin-3-ylamine was isolated by flash chromatography on silica gel eluting with EtOAc to 5% CH3OH in EtOAc (1.0 g, 86%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customsolids were removed from the reaction mixture by filtration
  3. customEvaporation of volatiles in vacuo
  4. customgave a solid
  5. customthat was triturated with toluene
  6. customRemoval of solids
  7. filtrationby filtration
  8. customfollowed by evaporation of volatiles in vacuo
  9. customgave a heavy oil

Sources & evidence

ORD record
ord-11d50723279c46cb8c8568d2322844a3
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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