1,3-Propanediol → HCID 33732116, compound

HRID 853886Notes

Reaction equation

HRID 853886 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[O:14])([O-:3])=[O:2].[CH2:15](O)[CH2:16][CH2:17][OH:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]12[O:18][CH2:17][CH2:16][CH2:15][O:14]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 521998p-Toluenesulfonic acid monohydrateHCID 46692505-Nitroisatin

Product 1

HCID 33732116HCID 33732116, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-nitroisatin (5.00 g, 26.0 mmol), 1,3 propandiol (4.76 mL , 65 mmol, 2.5 eq) and p-toluenesulfonic acid mono-hydrate (0.989 g, 5.2 mmol, 0.2 mol %)) in benzene (500 mL) was refluxed with a Dean Stark Trap for 23 hr. The benzene was decanted off and concentrated. The crude product was purified on Biotage KP silica gel eluting with 50/50 petroleum ether/EtOAc to give the title compound as an off white solid (1.78 g, 27% yield). NMR (300 Mz, DMSO-d6): consistent.

Workup

  1. temperaturewas refluxed with a Dean Stark Trap for 23 hr
  2. customThe benzene was decanted off
  3. concentrationconcentrated
  4. customThe crude product was purified on Biotage KP silica gel eluting with 50/50 petroleum ether/EtOAc

Sources & evidence

ORD record
ord-6d5e0445a39b443c9aca75ede868acc7
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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