Methane → HCID 12799993, compound

HRID 2412630Notes

Reaction equation

HRID 2412630 reaction equation
[CH2:1]([CH:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([O:23]C)=[O:22])=[CH:18][CH:19]=2)[NH:14][CH2:13]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[OH-].[K+].C>C(O)C.O>[CH2:1]([CH:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([OH:23])=[O:22])=[CH:18][CH:19]=2)[NH:14][CH2:13]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 297MethaneHCID 14797Potassium HydroxideHCID 12799984HCID 12799984, compound

Product 1

HCID 12799993HCID 12799993, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(RS)-Methyl 3-(n-undecyl)indoline-6-carboxylate (12.4 g) in ethanol (350 ml), containing potassium hydroxide (3.33 g) and water (45 ml), was stirred and refluxed for 24 hours. The solvent was removed in vacuo to give an off-white solid. The solid was dissolved in water, and the solution was treated with charcoal and filtered through diatomaceous earth. Glacial acetic acid (50 ml) was slowly added to the stirred solution and an off-white solid was collected and recrystallised from ethyl acetate to give (RS)-3-(n-undecyl)indoline-6-carboxylic acid (11.9 g), in the form of a white solid, m.p. 107°-111° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe solvent was removed in vacuo
  3. customto give an off-white solid
  4. filtrationfiltered through diatomaceous earth
  5. additionGlacial acetic acid (50 ml) was slowly added to the stirred solution
  6. customan off-white solid was collected
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-d92d64acf9d94690948027ec7cc40734
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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