Hydrochloric Acid → HCID 19701612, compound

HRID 862082Notes

Reaction equation

HRID 862082 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21]COC)=[C:6]([CH:20]=1)[C:7]([C:9]1[C:14]([CH:15]2OCC[O:16]2)=[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:21])=[C:6]([CH:20]=1)[C:7]([C:9]1[C:14]([CH:15]=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19701591HCID 19701591, compound

Product 1

HCID 19701612HCID 19701612, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(5-chloro-2-methoxymethoxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine (3.41 g), hydrochloric acid (5.0 ml) and THF (35 ml) was stirred for 27 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, then the solvent was distilled off to leave 2-(5-chloro-2-hydroxybenzoyl)-3-formylpyridine (2.03 g) (Compound E-10). The physical properties and spectrum data are shown in Table 16 and Table 18.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract solution was washed with a saturated aqueous saline solution
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5418d09767f149eeb5fec7986f557707
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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