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2-Methyl-2-butene → 1-(3-chloropyridin-2-yl)-5-(methoxycarbonyl)-1H-pyrazole-3-carboxylic acid

HRID 1630672
Notes
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Reaction equation

HRID 1630672 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH:17]=[O:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.O.O.P([O-])(O)(O)=[O:22].[Na+].Cl([O-])=O.[Na+].CC(=CC)C>C(O)(C)(C)C.O>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([C:17]([OH:22])=[O:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 86661390HCID 86661390, compound

Product 1

HCID 665876291-(3-chloropyridin-2-yl)-5-(methoxycarbonyl)-1H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

2.00 g (7.53 mmol) of methyl 1-(3-chloropyridin-2-yl)-3-formyl-1H-pyrazole-5-carboxylate were dissolved in 18 ml of tert-butanol, and 5 ml of water were then added. After cooling to 0° C., 2.35 g (15.1 mmol) sodium dihydrogenphosphate dihydrate, 2.73 g (30.1 mmol) of sodium chlorite and 3.17 g (45.2 mmol) of 2-methyl-2-butene were added in succession. After 1 hour at 20° C., water was added and the mixture was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure (logP: 1.38)

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. customthe solvent was removed under reduced pressure (logP: 1.38)

Sources & evidence

ORD record
ord-0f4cb405141f4a00bc81c661fa70c4dd
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791139B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes