Sulfuric Acid → HCID 68486225, compound

HRID 1401455Notes

Reaction equation

HRID 1401455 reaction equation
[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6]([CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)O)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.S(=O)(=O)(O)O.[OH-].[K+]>>[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6]([CH:14]=[CH:15][C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 57876161HCID 57876161, compound

Product 1

HCID 68486225HCID 68486225, compound

Conditions

Temperature
5 °C

Procedure

2-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-p-tolylethanol (1 equiv.) is refluxed with 25% sulfuric acid for 2 h. The reaction mixture is cooled to 5° C. with an ice-water bath. KOH (15% aq. solution) is added dropwise to the reaction mixture until pH 9-10 is achieved. The reaction mixture is extracted with EtOAc. The combined organic layers are washed with water followed by brine, dried over sodium sulfate and evaporated under vacuum. The crude product is purified by column chromatography over silica gel (100-200 mesh) using a gradient of MeOH-EtOAc (0-10%).

Workup

  1. extractionThe reaction mixture is extracted with EtOAc
  2. washThe combined organic layers are washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe crude product is purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-cb6af0ab6b484a3eb6650a201a154518
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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