Water → 2-{[(1-Carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinic acid

HRID 1029779Notes

Reaction equation

HRID 1029779 reaction equation
[C:1]([C:4]([NH:9][CH2:10][C:11]1[N:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:12]=1[C:13]([O:15]CC)=[O:14])([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].[OH-].[Na+].O>CO.C(OCC)(=O)C.O1CCCC1>[C:1]([C:4]([NH:9][CH2:10][C:11]1[N:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:12]=1[C:13]([OH:15])=[O:14])([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2]

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14600682Ethyl 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinate

Product 1

HCID 146006872-{[(1-Carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinic acidYield 60.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.6 g of ethyl 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinate (0.0174 mol) in 30 mL of methanol containing 2 g of NaOH (0.05 mol) and 10 mL water is stirred at room temperature for two hours and 30 minutes. The reaction is concentrated in vacuo and redissolved in 30 mL water; adjustment of the pH to 4 with concentrated hydrochloric acid and concentration in vacuo gives a gum. This residue is dissolved in a mixture of ethyl acetate, tetrahydrofuran, and methanol, dried over MgSO4, and concentrated in vacuo to 6 g foam. Crystallization from methanol-ether affords 3.1 g product, mp 180°-181° C.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. dissolutionredissolved in 30 mL water
  3. concentrationadjustment of the pH to 4 with concentrated hydrochloric acid and concentration in vacuo
  4. customgives a gum
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo to 6 g foam
  7. customCrystallization from methanol-ether

Sources & evidence

ORD record
ord-70be36d3b0fb4a69bf2d2056772df41f
Source dataset
uspto-grants-1992_04
Patent number
US05103009

Reaction notes

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