Sodium Hydroxide → HCID 59830749, compound

HRID 1187371Notes

Reaction equation

HRID 1187371 reaction equation
[CH2:1]([C:5]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:6]=1[C:7]([O:9]CC)=[O:8])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO>[CH3:2][CH2:1][CH2:5][CH:6]([CH3:12])[CH3:7].[CH2:1]([C:5]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:6]=1[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59830723HCID 59830723, compound

Product 2

HCID 78922-MethylpentaneHCID 59830749HCID 59830749, compoundYield 172.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-butyl-6-chloronicotinate (395 mg, 1.63 mmol) was stirred in methanol (10 ml) and 2M sodium hydroxide (2 ml, 4 mmol) was added. The solution was stirred at room temperature for 16 hours. The solvent was evaporated and the residue taken up in ice/water (10 ml) and acidified with 2M HCl. The milky solution was extracted with dichloromethane (2×15 ml) and the combined extracts were dried over MgSO4, filtered and evaporated, trituration with isohexane gave 2-butyl-6-chloronicotinic acid (300 mg, 86%) as a white solid.

Workup

  1. customThe solvent was evaporated
  2. extractionThe milky solution was extracted with dichloromethane (2×15 ml)
  3. dry with materialthe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-62dd2c00880145688b0373c0702aa359
Source dataset
uspto-grants-2014_03
Patent number
US08673938B2

Reaction notes

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