Ammonium Chloride → HCID 21876045, compound

HRID 2077664Notes

Reaction equation

HRID 2077664 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=2)[C:6]([N+:19]([O-])=O)=[CH:5][CH:4]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:19][C:6]1[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=2)=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21876169HCID 21876169, compound

Product 1

HCID 21876045HCID 21876045, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 2-{4-[(6-methoxy-3-nitro-2-pyridinyl)amino]phenyl}ethanol (step 1, 3.52 g, 12.17 mmol), iron powder (3.4 g, 60.84 mmol) and ammonium chloride (325 mg, 6.08 mmol) in ethanol/water (v/v, 2:1, 90 mL) was heated at reflux temperature for 1 h. After cooling, the catalyst was removed and the filtrate was concentrated. The residue was extracted with ethyl acetate (100 mL) and washed with water. The organic layer was dried (MgSO4), and concentrated to give 3.41 g (quant.) of the title compound as a black oil: 1H-NMR (CDCl3) δ 7.48 (2H, d, J=8.4 Hz), 7.14 (2H, d, J=8.4 Hz), 7.04 (1H, d, J=8.2 Hz), 6.75 (1H, br.s), 6.13 (1H, d, J=8.2 Hz), 3.87 (3H, s), 3.83 (2H, t, J=6.6 Hz), 2.81 (2H, t, J=6.6 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. temperatureAfter cooling
  4. customthe catalyst was removed
  5. concentrationthe filtrate was concentrated
  6. extractionThe residue was extracted with ethyl acetate (100 mL)
  7. washwashed with water
  8. dry with materialThe organic layer was dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-82734eb97c7b4db3bc653091738d4581
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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