Sodium Hydroxide → HCID 12797256, compound

HRID 2412625Notes

Reaction equation

HRID 2412625 reaction equation
[OH-].[Na+].[CH2:3]([C:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([O:26]C)=[O:25])=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>O.CO>[CH2:3]([C:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]([OH:26])=[O:25])=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12799944HCID 12799944, compound

Product 1

HCID 12797256HCID 12797256, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium hydroxide (15 g) in water (100 ml) was added dropwise during 30 minutes to a refluxing solution of methyl 3-(n-dodecyl)indole-6-carboxylate (12.8 g prepared as hereinbefore described in Example 85) in methanol (800 ml). The mixture was stirred and refluxed for 12 hours. The mixture was then concentrated to 500 ml volume and water (400 ml) was added. After cooling to 0° C., a solid was collected and was dissolved in hot glacial acetic acid (300 ml). The solution was then poured into water (800 ml) and a solid was collected, washed with water (4×100 ml) and dried at 60° C. Recrystallisation of the solid from methanol gave 3-(n-dodecyl)indole-6-carboxylic acid (9.0 g), in the form of a white solid, m.p. 181°-184° C.

Workup

  1. temperaturerefluxed for 12 hours
  2. concentrationThe mixture was then concentrated to 500 ml volume and water (400 ml)
  3. additionwas added
  4. customa solid was collected
  5. dissolutionwas dissolved in hot glacial acetic acid (300 ml)
  6. additionThe solution was then poured into water (800 ml)
  7. customa solid was collected
  8. washwashed with water (4×100 ml)
  9. customdried at 60° C
  10. customRecrystallisation of the solid from methanol

Sources & evidence

ORD record
ord-834b81993ab3471e8f92c75f37581778
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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