Hydrochloric Acid → HCID 20089886, compound

HRID 258344Notes

Reaction equation

HRID 258344 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][C:12]([CH3:14])=O)[CH:5]=1)[CH3:2].Cl.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C>[CH2:1]([N:3]([CH2:15][CH3:16])[C:4]1[CH:5]=[C:6]2[C:7]([C:12]([CH3:14])=[CH:11][NH:10]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20089887HCID 20089887, compound

Product 1

HCID 20089886HCID 20089886, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

An intimate mixture of 46.5 g of N,N-diethyl-N'-acetonyl-m-phenylenediamine and 46.5 g of zinc chloride is heated slowly, in which process it starts to melt from 70° C. upwards and from 115° C. upwards the exothermic reaction has to be controlled by external cooling. After maintaining the temperature of 130° C. for 30 minutes, 250 ml of 1N hydrochloric acid are added dropwise in the course of 20 minutes, in which process the temperature stabilised at approximately 90° C. The brown emulsion is stirred for a further 1.5 hours at this temperature and is then rendered alkaline with 100 ml of concentrated sodium hydroxide solution. Ethyl acetate is added to the resultant suspension and the latter is filtered. The organic phase is separated off, active carbon is added to it and it is stirred for 1 hour at room temperature. After filtering and evaporating down, 23 g of 6-diethylamino-3-methylindole is obtained in the form of a brown oil.

Workup

  1. temperatureis heated slowly, in which process it
  2. customto melt from 70° C.
  3. customfrom 115° C. upwards the exothermic reaction
  4. customstabilised at approximately 90° C
  5. filtrationthe latter is filtered
  6. customThe organic phase is separated off
  7. additionactive carbon is added to it and it
  8. stirringis stirred for 1 hour at room temperature
  9. filtrationAfter filtering
  10. customevaporating down

Sources & evidence

ORD record
ord-396762982a1b4e27b68a1f8972908438
Source dataset
uspto-grants-1993_11
Patent number
US05266699

Reaction notes

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