Sodium Hydroxide → (+/-)-2-[2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-6-methyl-3-oxoheptanoic acid

HRID 1440307Notes

Reaction equation

HRID 1440307 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]3[CH:22]([C:28](=[O:34])[CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[C:23]([O:25]CC)=[O:24])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]3[CH:22]([C:28](=[O:34])[CH2:29][CH2:30][CH:31]([CH3:32])[CH3:33])[C:23]([OH:25])=[O:24])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9891305Ethyl 2-[2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-6-methyl-3-oxoheptanoate

Product 1

HCID 18983252(+/-)-2-[2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-6-methyl-3-oxoheptanoic acidYield 42.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 23 g of ethyl 2-[2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-6-methyl-3-oxoheptanoate in 235 cm3 of 98% sulphuric acid is stirred for 20 hours at a temperature of approximately 20° C. and is then poured into 1.5 kg of ice. The precipitate obtained is separated by filtration, washed with water to a pH=6 and dried in air. The solid obtained is taken up in 3.8 liters of distilled water and 480 cm3 of a 0.1N aqueous sodium hydroxide solution. The insoluble product is separated by filtration, the filtrate is acidified to a pH=3 by addition of a 0.1N aqueous hydrochloric acid solution. The precipitate obtained is separated by filtration, washed with distilled water and then with isopropyl ether and dried at 20° C. under reduced pressure (0.07 kPa). 9.2 g of (±)-2-[2-(7-chloro-1,8-naphthyridin-2-yl)-3 -oxo-1-isoindolinyl]-6-methyl-3-oxoheptanoic acid, melting at 176° C., are thus obtained.

Workup

  1. customThe precipitate obtained
  2. customis separated by filtration
  3. washwashed with water to a pH=6
  4. customdried in air
  5. customThe solid obtained
  6. customThe insoluble product is separated by filtration
  7. additionthe filtrate is acidified to a pH=3 by addition of a 0.1N aqueous hydrochloric acid solution
  8. customThe precipitate obtained
  9. customis separated by filtration
  10. washwashed with distilled water
  11. dry with materialwith isopropyl ether and dried at 20° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-b031ed52201144948626a4e5a21f34ae
Source dataset
uspto-grants-1996_03
Patent number
US05498716

Reaction notes

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