Water → HCID 12799960, compound

HRID 2412640Notes

Reaction equation

HRID 2412640 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[C:21]([C:26]([O:28][CH3:29])=[O:27])[CH:20]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O.[OH-].[Na+].CN(C)[CH:35]=[O:36]>C(O)(=O)C>[CH:35]([C:25]1[C:24]2[C:19](=[CH:20][C:21]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:23]=2)[NH:18][C:17]=1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:36]

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 12799916HCID 12799916, compound

Product 1

HCID 12799960HCID 12799960, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of phosphorus oxychloride (20 ml) in dimethylformamide (80 ml) was added to a solution of methyl 2-(n-undecyl)indole-6-carboxylate (58.3 g) in dimethylformamide (250 ml) and the mixture was stirred at a temperature of 55°-90° C. for 2 hours. After cooling, the mixture was poured into rapidly stirred water. Aqueous sodium hydroxide (50% w/v) was added until pH 12, the mixture was stirred for 10 minutes, and then glacial acetic acid was added to pH 5. The mixture was stirred until the gummy product solidified. The solid was then collected and recrystallised from ethanol to give methyl 3-formyl-2-(n-undecyl)indole-6-carboxylate (52.5 g), in the form of a buff powder, m.p. 147°-149° C.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture was stirred for 10 minutes
  3. stirringThe mixture was stirred until the gummy product
  4. customThe solid was then collected
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-06b177fdb7d949fcabf21f235496684b
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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