Water → 5-Phenoxypyridin-2-amine

HRID 1966206Notes

Reaction equation

HRID 1966206 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][N:5]=1)([O-])=O.O>C(O)(=O)C.[Zn]>[O:10]([C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[N:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 962WaterHCID 221794212-Nitro-5-phenoxypyridine

Product 1

HCID 221794545-Phenoxypyridin-2-amineYield 90%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

8.2 2-Nitro-5-phenoxy-pyridine (11.3 mmol) is dissolved in acetic acid (30 ml) at 35° C. After addition of water (30 ml), zinc powder (6 eq.) is added and the reaction suspension is heated to 105° C. for 2.5 h. The reaction suspension is cooled to RT and filtrated. The filtrate is poured into 3.5% NaOH (700 ml) and extracted with dichloromethane. The combined organic phases are extracted with brine, dried over MgSO4 and the solvent is removed in vacuo. 5-Phenoxy-pyridin-2-ylamine is obtained as a pink powder in a yield of 90%; HPLC (method C): 1.32 min, LC-MS (method A): 0.531 min, 187.15 (M+H+).

Workup

  1. additionis added
  2. temperatureThe reaction suspension is cooled to RT
  3. filtrationfiltrated
  4. additionThe filtrate is poured into 3.5% NaOH (700 ml)
  5. extractionextracted with dichloromethane
  6. extractionThe combined organic phases are extracted with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-fbc2c413f0414773bca06d1c15580985
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

Loading…