Hydrochloric Acid → HCID 19701583, compound

HRID 862084Notes

Reaction equation

HRID 862084 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18]COC)=[C:6]([CH:17]=1)[C:7]([C:9]1[C:14]([C:15]#[N:16])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8].Cl.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([CH:17]=1)[C:7]([C:9]1[C:14]([C:15]#[N:16])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19701593HCID 19701593, compound

Product 1

HCID 19701583HCID 19701583, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(5-chloro-2-methoxymethoxybenzoyl)-3-cyanopyridine (1.50 g), hydrochloric acid (2.5 ml) and THF (17.5 ml) was stirred for 13 hours at room temperature. The reaction mixture was neutralized with an aqueous solution of sodium hydroxide, followed by extraction with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and dried (anhydrous sodium sulfate), which was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give 2-(5-chloro-2-hydroxybenzoyl)-3-cyanopyridine (1.10 g) (Compound E-13). The physical properties and spectrum data are shown in Table 16 and Table 19.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract solution was washed with a saturated aqueous saline solution
  3. dry with materialdried (anhydrous sodium sulfate), which
  4. customwas purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a892fcd7c6ee43a89e6f20303667f783
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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