Hydrochloric Acid → HCID 24823891, compound

HRID 1925358Notes

Reaction equation

HRID 1925358 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2.C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.Cl>CS(C)=O.O>[N:26]1[CH:27]=[CH:28][C:23]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]3)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 818524-Chloropyridine hydrochlorideHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 24823891HCID 24823891, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 6-hydroxy-1-napthoic acid (2 g, 10.6 mmol) in DMSO (5 mL), Cs2CO3 (14 g, 42.4 mmol) was added and stirred at RT 10 min. 4-Chloropyridine hydrochloride (1.9 g, 12.7 mmol) was added in one portion and the reaction mixture heated to 140° C. for 12 h. The reaction mixture was cooled to RT, diluted with water and made pH 5 using 6 N HCl, at which point a brown precipitate crashed out. The solid was filtered and rinsed with water and hexanes to yield the title compound.

Workup

  1. temperaturethe reaction mixture heated to 140° C. for 12 h
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationThe solid was filtered
  4. washrinsed with water and hexanes

Sources & evidence

ORD record
ord-8c8c87e34ecf48f7a1aa05a6435893ba
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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