Hydrochloric Acid → HCID 21709044, compound

HRID 651771Notes

Reaction equation

HRID 651771 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:12]=2)[N:7]([CH3:19])[CH:6]=1.[OH-].[Na+].Cl>CO>[CH3:19][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:9]=2)[C:5]([CH2:4][C:3]([OH:20])=[O:2])=[CH:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70118148HCID 70118148, compound

Product 1

HCID 21709044HCID 21709044, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(1-Methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)acetic acid methyl ester (360 mg, 1.32 mmol) and NaOH (132 mg, 3.3 mmol) in methanol (8 mL) were heated at reflux for 30 min. The reaction mixture was cooled to 0° C. and acidified using 1 N HCl. The mixture was extracted with EtOAc (3×100 mL) and CH2Cl2 (3×100 mL). The combined organic extracts were dried (MgSO4) and concentrated. Chromatography of the crude product over silica gel using 5-20% MeOH in CH2Cl2 gave (1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)acetic acid (241 mg, 71%).

Workup

  1. temperatureat reflux for 30 min
  2. extractionThe mixture was extracted with EtOAc (3×100 mL) and CH2Cl2 (3×100 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80bf13dcdd2f43d2b4d89485331079f0
Source dataset
uspto-grants-2001_08
Patent number
US06281356B1

Reaction notes

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