Glycerol → HCID 67115982, compound

HRID 576681Notes

Reaction equation

HRID 576681 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:9].[Na+].[I-].O[CH2:13][CH:14]([CH2:16]O)O.[OH-].[Na+]>OS(O)(=O)=O>[NH2:8][C:7]1[C:2]([Cl:1])=[C:3]2[C:4]([CH:13]=[CH:14][CH:16]=[N:9]2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 753GlycerolHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 124029782-Chloro-m-phenylenediamine

Product 1

HCID 67115982HCID 67115982, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 2-chlorobenzene-1,3-diamine (24 mmol) (CAS 6400-14-2) and NaI (150 mg) in 80% H2SO4 (20 g) was added Glycerol (45 g). The mixture was stirred at 150° C. to 170° C. for 5 h. The mixture was cooled to room temperature. Aqueous 5N NaOH was used to adjust the pH to alkaline, which was then extracted with EtOAc washed with brine, dried over MgSO4 and concentrated under reduced vacuum. Flash column chromatography (EtOAc:Hexane) yielded 7-amino-8-chloroquinoline (800 mg), as a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ: 8.69 (dd, J=4.4, 1.8 Hz, 1H), 8.13 (dd, J=7.9, 1.8 Hz, 1H), 7.61 (d, J=9.1 Hz, 1H), 7.14-7.29 (m, 2H)

Workup

  1. extractionwhich was then extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced vacuum

Sources & evidence

ORD record
ord-0117d3f708254479bdfa46aaeb992e59
Source dataset
uspto-grants-2015_05
Patent number
US09040532B2

Reaction notes

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