Ethyl Acetate → HCID 24823895, compound

HRID 2115828Notes

Reaction equation

HRID 2115828 reaction equation
Cl.[CH3:2][NH2:3].Cl[C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([C:22]([OH:24])=[O:23])=[CH:17][CH:16]=[CH:15]3)[CH:8]=[CH:7][N:6]=1.CCOC(C)=O>O>[CH3:2][NH:3][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([C:22]([OH:24])=[O:23])=[CH:17][CH:16]=[CH:15]3)[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 6364545Methylamine hydrochlorideHCID 24823893HCID 24823893, compound

Product 1

HCID 24823895HCID 24823895, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To melted methylamine hydrochloride (Aldrich, 73.7 g, 1090 mmol) at 235° C. (oil bath) was added 6-(2-chloropyridin-4-yloxy)-1-naphthoic acid (6.54 g, 21.8 mmol). The reaction mixture was stirred for 3 min and cooled to RT. The brownish solid was treated with EtOAc and water and stirred until all residue was either in solution or suspended. The precipitate was filtered off, washed with EtOAC and purified by silica gel chromatography using 0-100% of a 85:15:0.5 mixture of DCM:MeOH:AcOH. The product obtained was washed with water, filtered and dried under vacuum to give the title compound.

Workup

  1. customat 235° C.
  2. stirringstirred until all residue
  3. filtrationThe precipitate was filtered off
  4. washwashed with EtOAC
  5. custompurified by silica gel chromatography
  6. addition0-100% of a 85:15:0.5 mixture of DCM
  7. customThe product obtained
  8. washwas washed with water
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-222428b181b74e57b124f0303e84a5ec
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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