Hydrochloric Acid → HCID 59512399, compound

HRID 1158387Notes

Reaction equation

HRID 1158387 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH3:19])=[CH:10][N:11]2[CH2:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl.C(Cl)Cl>CO.O>[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)[C:9]([CH3:19])=[CH:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 675419721-(3-Methoxy-propyl)-3-methyl-1H-indole-6-carboxylic acid methyl ester

Product 1

HCID 59512399HCID 59512399, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carboxylic acid methyl ester (1.56 g, 6.3 mmol) in MeOH (20 mL) and H2O (1 mL) is added NaOH (756 mg, 18.9 mmol) and the mixture is stirred at 50° C. overnight. Then neutralized by the addition of water and HCl 1.0 M (3 eq, 18.9 mmol). CH2Cl2 is added, the layers are separated, and the aqueous one is extracted twice with CH2Cl2. The combined organic layers are dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material is obtained in a pure form and is used in the next step without purification. MS (LC-MS): 248.0 [M+H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.93 min.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous one is extracted twice with CH2Cl2
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c073ffabeca843be82aa6cdd79dcdd84
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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