Hydrochloric Acid → 5-Chloropyridine-2-carboxaldehyde

HRID 1791356Notes

Reaction equation

HRID 1791356 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.C(O)C.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27628725-Chloro-2-picolinic acid

Product 1

HCID 101032675-Chloropyridine-2-carboxaldehydeYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 76.3%) was obtained obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid (200 mg, 1.03 mmol) with ethanol (3 mL) and 4M HCl in dioxane (0.5 mL) at 90° C. for 20 h. 5-Chloro-pyridine-2-carbaldehyde (58 mg, 52%) was obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 0.786 mmol) with 1 M DIBAL in toluene (1.74 mL, 1.74 mmol) in dichloromethane (4.0 mL) 20 min. GC-MS (M+): 141

Workup

  1. customobtained

Sources & evidence

ORD record
ord-5c1c154152fe45b2afb28915615593be
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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