Hydrochloric Acid → HCID 12797216, compound

HRID 2412589Notes

Reaction equation

HRID 2412589 reaction equation
[C:1]([NH:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[CH3:28])[C:22]([OH:24])=[O:23])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CC(C)([O-])C.[K+].Cl>O>[CH2:2]([C:1]1[NH:18][C:19]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[C:21]([C:22]([OH:24])=[O:23])[CH:20]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12797215HCID 12797215, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 12797216HCID 12797216, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(n-hexadecanamido)-4-methylbenzoic acid (6.0 g) and potassium tert-butoxide (22.0 g) was placed in a preheated Woods Metal bath (temperature range 240°-260° C.). The temperature of the bath was rapidly raised to between 290° and 305° C. and was maintained within this region for 15 minutes. The mixture was then left to cool to room temperature. Water (100 ml) was added to the mixture and the resultant suspension was treated with dilute hydrochloric acid (100 ml of strength 2N) and the mixture was extracted with diethyl ether (3×100 ml). The organic extract was washed with water (2×100 ml), dried over magnesium sulphate and was evaporated in vacuo to give a solid. The solid was recrystallised from glacial acetic acid and then toluene to give 2-(n-pentadecyl)indole-6-carboxylic acid (3.05 g), in the form of an off-white solid, m.p. 140°-142° C.

Workup

  1. customwas placed in a preheated Woods Metal bath
  2. custom(temperature range 240°-260° C.)
  3. temperatureThe temperature of the bath was rapidly raised to between 290° and 305° C.
  4. temperaturewas maintained within this region for 15 minutes
  5. waitThe mixture was then left
  6. extractionthe mixture was extracted with diethyl ether (3×100 ml)
  7. extractionThe organic extract
  8. washwas washed with water (2×100 ml)
  9. dry with materialdried over magnesium sulphate
  10. customwas evaporated in vacuo
  11. customto give a solid
  12. customThe solid was recrystallised from glacial acetic acid

Sources & evidence

ORD record
ord-0b82fbac88a9482e8e4e5cdcc9589879
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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