Sodium Hydroxide → HCID 22622501, compound

HRID 1604354Notes

Reaction equation

HRID 1604354 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19]C)=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10].[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22622509HCID 22622509, compound

Product 1

HCID 22622501HCID 22622501, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of methyl 2-[N-(5-bromo-2-(cyclopentylmethoxy)benzyl)-N-ethylamino]pyridine-5-carboxylate (see reference example 5) (0.37 g, 0.83 mmol) in THF (4 ml) and methanol (4 ml) was treated with 1N aqueous sodium hydroxide solution (4 ml). The reaction was heated at 40° C. for 18 hours. The solvents were evaporated at reduced pressure and the residue was acidified with IN acetic acid (4 ml) and allowed to stir for 2 days. The precipitate was filtered, washed with water and dried in vacuo at 45° C. to give the title compound as a white solid (0.32 g, 89%).

Workup

  1. customThe solvents were evaporated at reduced pressure
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-bfb3323a642a400b89d633680e636464
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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