Hydrochloric Acid → HCID 12799929, compound

HRID 2412610Notes

Reaction equation

HRID 2412610 reaction equation
[CH2:1]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([OH:23])=[O:22])[CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl.[CH2:25](O)[CH3:26]>>[CH2:1]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([O:23][CH2:25][CH3:26])=[O:22])[CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 12797236HCID 12797236, compound

Product 1

HCID 12799929HCID 12799929, compound

Procedure

A solution of 2-(n-undecyl)indole-6-carboxylic acid (11.9 g) in ethanol (50 ml) containing a solution of hydrogen chloride gas in ethanol (75 ml, of strength 39% w/v) was refluxed for 4.5 hours. The solution was cooled and a solid was collected which was dissolved in diethyl ether, and the ethereal solution was washed with water (2×100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo to give a residue which was recrystallised from methanol to give ethyl 2-(n-undecyl)indole-6-carboxylate (6.2 g), in the form of very pale yellow needles, m.p. 84°-86° C.

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. temperatureThe solution was cooled
  3. customa solid was collected which
  4. dissolutionwas dissolved in diethyl ether
  5. washthe ethereal solution was washed with water (2×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed in vacuo
  8. customto give a residue which
  9. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-7902ce3b0ece4fe8a962ca141c982550
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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