Hydrochloric Acid → 2-Benzyloxy-4-phenoxyphenylamine

HRID 1642624Notes

Reaction equation

HRID 1642624 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:22]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[In].Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[NH2:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5359967IndiumHCID 598727722-Benzyloxy-4-phenoxy-1-nitrobenzene

Product 1

HCID 667569242-Benzyloxy-4-phenoxyphenylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-benzyloxy-4-phenoxy-1-nitrobenzene (1.0 g, 3.12 mmol) and indium powder (1.0 g, 8.7 mmol) in THF (8 mL) is added concentrated HCl (1.5 mL) dropwise. The mixture is stirred at ambient temperature for 2.5 h. The solution is decanted from unreacted indium and 2N NaOH is added, which results in the formation of a gummy precipitate. The residue is triturated with EtOAc and centrifuged. The solution is decanted and the solvent removed under reduced pressure to afford a dark oil. The residue is purified by flash chromatography using DCM to elute 2-benzyloxy-4-phenoxyphenylamine as an oil: 1H NMR (CDCl3) δ 7.43-7.23 (m, 8H), 7.00 (t, 1H), 6.92-6.88 (m, 1H), 6.69 (d, J=8.33 Hz, 1H), 6.63 (d, J=2.52 Hz, 1H), 6.51 (dd, J=8.34, 2.52 Hz, 1H), 5.00 (s, 2H), 3.71 (br s, 2H); MS (M+H)+=292.

Workup

  1. customThe solution is decanted from unreacted indium and 2N NaOH
  2. additionis added
  3. customwhich results in the formation of a gummy precipitate
  4. customThe residue is triturated with EtOAc
  5. customThe solution is decanted
  6. customthe solvent removed under reduced pressure
  7. customto afford a dark oil
  8. customThe residue is purified by flash chromatography
  9. washto elute 2-benzyloxy-4-phenoxyphenylamine as an oil

Sources & evidence

ORD record
ord-eeb2fe6b3f594a23bd0e50e02144b7de
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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