Ammonium Chloride → 4-(Pyridin-2-ylmethoxy)aniline

HRID 1947622Notes

Reaction equation

HRID 1947622 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 8209312-[(4-Nitrophenoxy)methyl]pyridine

Product 1

HCID 104427734-(Pyridin-2-ylmethoxy)anilineYield 86.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

2-[(4-Nitrophenoxy)methyl]pyridine (2.30 g, 10 mmol) was dissolved in ethanol (160 mL) and water (40 mL). NH4Cl (5.30 g) was added to the above mixture and heated to 70-80° C. To this reaction mixture was added iron powder (5.50 g) in portion wise manner under a vigorous stirring and the stirring was continued for 2 h. The reaction mixture was filtered through a Celite pad when hot and washed the filter bed with MeOH. The filtrate was concentrated, diluted with water, extracted with CH2Cl2 (3×75 mL), dried and concentrated to provide 2-[(4-aminophenoxy)methyl]pyridine as brown solid (1.735 g) in 86% yield. 1H NMR (CDCl3): δ 8.56 (m, 1H), 7.67 (m, 1H), 7.49 (d, 1H, J=7.8 Hz), 7.18 (m, 1H), 6.80 (d, 2H, J=8.7 Hz), 6.62 (d, 2H, J=8.7 Hz), 5.12 (s, 2H), 3.43 (br s, 2H); LCMS (m/z): 201 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad when hot
  2. washwashed the filter bed with MeOH
  3. concentrationThe filtrate was concentrated
  4. additiondiluted with water
  5. extractionextracted with CH2Cl2 (3×75 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-039f6b091a204d75a3aedab96a6ec6d7
Source dataset
uspto-grants-2013_03
Patent number
US08399472B2

Reaction notes

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