Water → HCID 12799962, compound

HRID 2412645Notes

Reaction equation

HRID 2412645 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([C:22]([O:24][CH3:25])=[O:23])[CH:16]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O.[OH-].[Na+].CN(C)[CH:31]=[O:32]>C(O)(=O)C>[CH:31]([C:21]1[C:20]2[C:15](=[CH:16][C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=2)[NH:14][C:13]=1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:32]

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 12799918HCID 12799918, compound

Product 1

HCID 12799962HCID 12799962, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of phosphorus oxychloride (35 ml) in dimethylformamide (150 ml) was added to a solution of methyl 2-(n-heptyl)indole-6-carboxylate (67.5 g) in dimethylformamide (250 ml) and the resulting solution was stirred at between 70° and 85° C. for 2 hours. The mixture was then stirred for 30 minutes while the temperature dropped to 50° C. and was then poured into water (2 liters). Ice was added to reduce the temperature to 25° C. and a 50% w/v aqueous sodium hydroxide solution was added until the pH reached 11. After stirring for 10 minutes, acetic acid was added to pH 5 and the mixture was stirred until the product has solidified. Recrystallisation from methanol yielded methyl 3-formyl-2-(n-heptyl)indole-6-carboxylate (65.0 g) in the form of colourless, lustrous needles, m.p. 177°-180° C.

Workup

  1. stirringThe mixture was then stirred for 30 minutes while the temperature
  2. additiondropped to 50° C.
  3. additionIce was added
  4. customto 25° C.
  5. stirringAfter stirring for 10 minutes
  6. stirringthe mixture was stirred until the product
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-7855efc289dc48df800e0c24a2de3d72
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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