2-[1-(2-Chloro-4-nitrophenoxy)-1-methylethyl]pyridine → 3-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)aniline

HRID 1864360Notes

Reaction equation

HRID 1864360 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:7])[CH3:6]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:17]=[C:16]([CH:15]=[CH:14][C:3]=1[O:4][C:5]([CH3:7])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:6])[NH2:18]

Participants

3

Reactant 1

HCID 690597022-[1-(2-Chloro-4-nitrophenoxy)-1-methylethyl]pyridine

Product 1

HCID 690590593-Chloro-4-(1-methyl-1-pyridin-2-ylethoxy)anilineYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[1-(2-Chloro-4-nitrophenoxy)-1-methylethyl]pyridine (800 mg, 2.74 mmol) was dissolved in ethyl acetate (50 ml). The mixture was purged with nitrogen, and platinum on activated carbon (10%, 100 mg) was added. The mixture was hydrogenated for 6 hours using a burette filled with hydrogen. The system was degassed and purged with nitrogen, and the catalyst removed by filtration. The filtrate was concentrated in vacuo, and the residue purified by chromatography, eluting with 20% to 30% ethyl acetate in iso-hexane. The appropriate fractions were evaporated to give 3-chloro-4-(1-methyl-1-pyridin-2-ylethoxy)aniline as a straw-coloured oil (452 mg, 63%); NMR Spectrum (DMSO-d6, 400 MHz, CDCl3) 1.63 (s, 6H), 3.41 (bs, 2H), 6.25 (dd, 1H), 6.35 (d, 1H), 6.65 (d, 1H), 7.11 (ddd, 1H), 7.63 (ddd, 1H), 7.77 (d, 1H), 8.50 (d, 1H).

Workup

  1. customThe mixture was purged with nitrogen, and platinum on activated carbon (10%, 100 mg)
  2. additionwas added
  3. additionfilled with hydrogen
  4. customThe system was degassed
  5. custompurged with nitrogen
  6. customthe catalyst removed by filtration
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue purified by chromatography
  9. washeluting with 20% to 30% ethyl acetate in iso-hexane
  10. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-07c5e94403a14068829e51ca46131dc4
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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