Methanol → HCID 23003155, compound

HRID 396196Notes

Reaction equation

HRID 396196 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:25][CH2:26][CH2:27][C:28]#[N:29])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])=[CH:10][CH:9]=2)=[O:5])C.CO.[OH-].[Na+]>O1CCCC1>[C:28]([CH2:27][CH2:26][CH2:25][N:7]1[C:8]2[C:13](=[CH:12][C:11]([O:15][CH2:16][C:17]3[C:18]([Cl:24])=[CH:19][CH:20]=[CH:21][C:22]=3[Cl:23])=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([OH:5])=[O:3])#[N:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 70030611HCID 70030611, compound

Product 1

HCID 23003155HCID 23003155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Cyanopropyl)-5-(2,6-dichlorobenzyloxy)-1H-indole-2-carboxylic acid ethyl ester (1.89 g, 4.38 mmol), from Example 1(c), was dissolved in tetrahydrofuran (5 mL). Methanol (5 mL) and 1.0 N NaOH (5 mL) were added and the reaction mixture was stirred at ambient temperature for 12 h. The tetrahydrofuran and methanol were removed under reduced pressure and water (10 mL) was added. The solution was acidified to pH 2 with 10% aqueous HCl solution. The product precipitated as a white solid (1.52 g, 86%) and was collected through vaccuum filtration. (MS(ES) m/e 403.0 [M +H]+.

Workup

  1. customThe tetrahydrofuran and methanol were removed under reduced pressure and water (10 mL)
  2. additionwas added
  3. customThe product precipitated as a white solid (1.52 g, 86%)
  4. filtrationwas collected through vaccuum filtration

Sources & evidence

ORD record
ord-bbd90716d7f543668334fb35ae9796b5
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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