Sodium Hydroxide → HCID 59512416, compound

HRID 1158410Notes

Reaction equation

HRID 1158410 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH2:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[CH3:18][O:17][CH2:16][CH2:15][CH2:14][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=2)[CH:9]=[CH:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67542758methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate

Product 1

HCID 59512416HCID 59512416, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-methoxy-propyl)-1H-indole-6-carboxylic acid methyl ester (7 g, 28.5 mmol) in MeOH (50 mL) is added NaOH 2N (28.5 mL), and the mixture is stirred for 3 h. The solvent is concentrated and the remaining aqueous residue is acidified with HCl 1N and extracted twice with CH2Cl2. The combined organic extracts are dried over Na2SO4, filtered and concentrated to give title product. TLC, Rf (c-hexane/AcOEt 2:1)=0.25. MS (LC-MS): 232.0 [M+H]+, tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, flow: 1.5 ml/min): 5.04 min.

Workup

  1. concentrationThe solvent is concentrated
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-92bfe03239f24d70ba946d9f20342e53
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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