Sodium Hydroxide → [4-(7-Chloro-1-oxo-1,2-dihydro-isoquinolin-6-yloxy)-piperidin-1-yl]-acetic acid

HRID 2059584Notes

Reaction equation

HRID 2059584 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][C:22]=2[Cl:23])[C:19](=[O:24])[NH:18][CH:17]=[CH:16]3)[CH2:8][CH2:7]1)C.[OH-].[Na+]>CO>[Cl:23][C:22]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][NH:18][C:19]2=[O:24])=[CH:14][C:13]=1[O:12][CH:9]1[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:25])=[O:3])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59229774[4-(7-Chloro-1-oxo-1,2-dihydro-isoquinolin-6-yloxy)-piperidin-1-yl]-acetic acid ethyl ester

Product 1

HCID 59229772[4-(7-Chloro-1-oxo-1,2-dihydro-isoquinolin-6-yloxy)-piperidin-1-yl]-acetic acidYield 59.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.56 g (4.27 mmol) [4-(7-Chloro-1-oxo-1,2-dihydro-isoquinolin-6-yloxy)-piperidin-1-yl]-acetic acid ethyl ester (41) were dissolved in 20 mL of methanol and 20 ml of 2N NaOH were added. After stirring for 1 h at room temperature, the solvent was removed i. vac. and the residue was dissolved in water. The aqueous solution was neutralized by adding 2 N HCl. Filtration of the precipitate and drying gave 856 mg of the title compound. Rt=0.82 min (Method B). Detected mass: 337.1 (M+H+).

Workup

  1. customthe solvent was removed i
  2. dissolutionand the residue was dissolved in water
  3. additionby adding 2 N HCl
  4. filtrationFiltration of the precipitate
  5. customdrying

Sources & evidence

ORD record
ord-45b9030d93c5416ab4974e38ef3e7cfa
Source dataset
uspto-grants-2012_10
Patent number
US08278294B2

Reaction notes

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