Stannous chloride dihydrate → HCID 90415269, compound

HRID 1776728Notes

Reaction equation

HRID 1776728 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[N+:15]([O-])=O)=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl>C(O)C>[NH2:15][C:9]1[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:8]=1[NH:7][CH2:6][C:5]1[CH:18]=[CH:19][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 43750805HCID 43750805, compound

Product 1

HCID 90415269HCID 90415269, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-((4-bromobenzyl)amino)-3-nitrophenol (20 g, 63 mmol) in ethanol (200 mL) was added SnCl2.2H2O (71 g, 314 mmol) and the resulting mixture stirred at 90° C. for 1 h. The mixture was cooled to RT and concentrated to dryness. The aqueous residue was then treated with sat. aq. NaHCO3 to ˜pH 7 and extracted with DCM (5×1 L). The organics were combined, dried (Na2SO4), filtered and concentrated to dryness. The residue was purified by FCC to afford the title compound. 1H NMR (300 MHz, DMSO-d6) 8.17 (s, 1H), 7.48 (d, J=8.4, 2H), 7.30 (d, J=8.3, 2H), 6.11 (dd, J=17.2, 5.5, 2H), 5.90-5.74 (m, 1H), 4.54 (s, 2H), 4.48 (t, J=5.7, 1H), 4.13 (d, J=5.5, 2H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated to dryness
  3. additionThe aqueous residue was then treated with sat. aq. NaHCO3
  4. extractionextracted with DCM (5×1 L)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-b9122e71ecf748e8a499f38b98f0277b
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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