Water → HCID 53741601, compound

HRID 1439918Notes

Reaction equation

HRID 1439918 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:19]([O-])=O)[C:5]([CH2:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=O)=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[CH:7]=1.O>CC(C)=O>[CH3:18][O:17][C:15]([C:13]1[NH:19][C:4]2[C:5]([CH:12]=1)=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[O:16]

Participants

4

Reactant 2

HCID 962WaterHCID 18984726HCID 18984726, compound

Product 1

HCID 53741601HCID 53741601, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 3-chloro-5-(3-hydroxypropyl)-6-methoxalylmethylnitrobenzene (19.91 g, 0.063 mol) in acetone (300 mL) was added dropwise a mixture of 20% TiCl3 (340 g, 0.441 mol), water (300 mL), and acetone (300 mL) at room temperature over a period of 30 min. The mixture was stirred for 30 min at room temperature and extracted with AcOEt. The extracts were washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 4:1 to 1:2 hexane/toluene to give 11.39 g of the title compound (68%): 1H NMR (CDCl3) δ8.96 (bs, 1H), 7.27 (s, 1H), 7.26 (d, 1H, J=1.7 Hz), 6.97 (d, 1H, J=1.7 Hz), 3.95 (s, 3H), 3.71 (t, 2H, J=6.3 Hz), 2.98 (t, 2H, J=7.8 Hz), 2.00 (m, 2H).

Workup

  1. extractionextracted with AcOEt
  2. washThe extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 4:1 to 1:2 hexane/toluene

Sources & evidence

ORD record
ord-4120417df452420aa762aab3a9770863
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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