Sulfuric Acid → HCID 59454917, compound

HRID 1401471Notes

Reaction equation

HRID 1401471 reaction equation
[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6]([CH2:14][CH:15]([C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=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]=[N: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 57876025HCID 57876025, compound

Product 1

HCID 59454917HCID 59454917, compound

Conditions

Temperature
5 °C

Procedure

2-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-(6-methylpyridin-3-yl)ethanol (1 g, 2.98 mmol, 1 eq) was refluxed with 25% sulfuric acid (7 mL) for 2 h. The reaction mixture was cooled to 5° C. with an ice-water bath. KOH (15% aq. solution) was added dropwise to the reaction mixture until pH 9-10 was achieved. The reaction mixture was extracted with EtOAc (3×10 mL). The combined organic layers were washed with water (10 mL) followed by brine, dried over sodium sulfate and evaporated under vacuum. The crude product was purified by column chromatography over silica gel (100-200 mesh) using a gradient of MeOH-EtOAc (0-10%). 1H NMR (CD3OD, TFA salt) δ (ppm): 8.8 (s, 1H), 8.55 (d, 1H), 7.95 (d, 1H), 7.75 (m, 2H), 7.35 (s, 1H), 7.28 (d, 1H), 7.0 (d, 1H), 4.8 (bs, 1H), 4.4 (bs, 1H), 3.9 (bs, 1H), 3.6 (bs, 1H), 3.4 (t, 2H), 3.15 (s, 3H), 2.75 (s, 3H), 2.45 (s, 3H).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with water (10 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe crude product was purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-3d6898922c954fe7979fd05110fa78ad
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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