Hydrochloric Acid → HCID 11524645, compound

HRID 1821955Notes

Reaction equation

HRID 1821955 reaction equation
[OH:1][CH:2]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[OH-:31].[K+].Cl>C(O)(C)(C)C.O>[OH:1][CH:2]([CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:21][CH:22]=1)[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH2:14])=[O:31])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68843319HCID 68843319, compound

Product 1

HCID 11524645HCID 11524645, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

0.18 g (0.44 mmol) 1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-5-carbonitrile (Example 15A) is dissolved in 15 ml tert-butanol, mixed with 0.23 g (3.6 mmol) pulverized, 88% potassium hydroxide and heated under reflux for 11 h. Having cooled down, the mixture is hydrolyzed in water and acidified with 1N hydrochloric acid. Three extractions with diethyl ether, concentration to half the volume on the rotary evaporator, washing with water and with saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellowish solid which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 1:1) and yields the product as a solid.

Workup

  1. additionmixed with 0.23 g (3.6 mmol)
  2. temperatureunder reflux for 11 h
  3. temperatureHaving cooled down
  4. extractionThree extractions
  5. concentrationwith diethyl ether, concentration to half the volume
  6. customon the rotary evaporator
  7. washwashing with water and with saturated NaCl solution
  8. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  9. customleave as a crude product a yellowish solid which
  10. customis purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-91c858abc59c422ebce4a865f3b4bd66
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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