Sodium Hydroxide → HCID 22675495, compound

HRID 1006010Notes

Reaction equation

HRID 1006010 reaction equation
[CH2:1]([C:8]1[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=1[CH2:10][N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][N:15]=1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([C:8]1[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=1[CH2:10][N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][N:15]=1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22675552HCID 22675552, compound

Product 1

HCID 22675495HCID 22675495, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-[N-(2-(benzyl)benzyl)-N-ethylamino]-5-pyridinecarboxylate (0.9 g, 2.5 mmol) in THF (6 ml) and methanol (6 ml) were treated with 1N aqueous sodium hydroxide (7 ml), and stirred at ambient temperature overnight. The clear solution was evaporated to low bulk, treated with water and glacial acetic acid to pH 4. The resultant white precipitate was stirred for 15 minutes, filtered, washed well with water, then sucked dry to yield the title product as a white solid (0.8 g, 92%). MS: (M+H)+347 (M·)+346

Workup

  1. customThe clear solution was evaporated to low bulk
  2. additiontreated with water and glacial acetic acid to pH 4
  3. stirringThe resultant white precipitate was stirred for 15 minutes
  4. filtrationfiltered
  5. washwashed well with water
  6. customsucked dry

Sources & evidence

ORD record
ord-1a7667fd622e41afa6c2107e09beae0d
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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