Lithium hydroxide, monohydrate → 2-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid

HRID 1245765Notes

Reaction equation

HRID 1245765 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[Cl:17].O[Li].O>O.O1CCOCC1>[Cl:17][C:5]1[N:6]=[C:7]([CH3:16])[CH:8]=[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:4]=1[C:3]([OH:18])=[O:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 248068762-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester

Product 1

HCID 248066612-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by reaction of 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester with LiOH.H2O in a mixture of water and dioxane at room temperature. The desired product was acidified to pH 3 and extracted with ethyl acetate. The organic layer was dried and concentrated to dryness. The title compound was obtained as white crystals after titration with ethyl acetate. mp. 164–165° C.; anal. For C12H17Cl2O2 cacl. C, 56.14; H, 6.67; N, 10.91; found: C, 56.40; H, 6.53; H, 10.93.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d79ec4356cb74edda82b61aac3d737ae
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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