2-Chloro-5-((2,2-dimethyl-1-oxopropyl)amino)-beta-hydroxy-4-pyridine propanoic acid, 1,1-dimethylethyl ester → 6-Chloro-1,7-naphthyridin-2(1H)-one

HRID 485198Notes

Reaction equation

HRID 485198 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](C(O)CC(OC(C)(C)C)=O)[C:5]([NH:18][C:19](=[O:24])[C:20]([CH3:23])(C)C)=[CH:4][N:3]=1.[H][H]>O1CCOCC1.Cl.O>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][N:3]=1)[NH:18][C:19](=[O:24])[CH:20]=[CH:23]2

Participants

6

Reactant 2

HCID 155923722-Chloro-5-((2,2-dimethyl-1-oxopropyl)amino)-beta-hydroxy-4-pyridine propanoic acid, 1,1-dimethylethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 155923736-Chloro-1,7-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.63 g (13 mmoles) of 2-chloro-5-((2,2-dimethyl-1-oxopropyl)amino)-β-hydroxy-4-pyridine propanoic acid, 1,1-dimethylethyl ester in 70 ml of dioxane and 30 ml of 3N HCl in water was warmed at reflux for a period of 4 hours. The solution was diluted with 100 ml of water and cooled to give a white precipitate. The crystals were filtered, washed with water and dried in a vacuum oven to give 2.18 g (93% of theoretical) of the above-captioned compound having a melting point of 304°-306° C. The carbon, hydrogen and nitrogen content calculated for C8H5ClN2O is C, 53.20; H, 2.79; and N, 15.52 percent by weight which compares to that actually found upon analysis of C, 53.55; H, 2.79; and N, 15.47.

Workup

  1. temperatureat reflux for a period of 4 hours
  2. temperaturecooled
  3. customto give a white precipitate
  4. filtrationThe crystals were filtered
  5. washwashed with water
  6. customdried in a vacuum oven
  7. customto give 2.18 g (93% of theoretical) of the above-captioned compound

Sources & evidence

ORD record
ord-ba1d45f7e6e4494d9d0ed17155651741
Source dataset
uspto-grants-1985_08
Patent number
US04536208

Reaction notes

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