Hydrochloric Acid → 3-(2-Aminoethyl)-5-methoxy-6,7-dichloroindol-2-carboxylic acid

HRID 65483Notes

Reaction equation

HRID 65483 reaction equation
[O:1]=[C:2]1[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][NH:3]1)=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[C:10]=3[Cl:18].[OH-:19].[K+].Cl>C(O)C.O>[NH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[C:10]([Cl:18])[C:11]([Cl:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C:7]=1[C:2]([OH:19])=[O:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 136906441-oxo-6-methoxy-7,8-dichloro-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

Product 1

HCID 136906453-(2-Aminoethyl)-5-methoxy-6,7-dichloroindol-2-carboxylic acidYield 96.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The above lactam was hydrolyzed with base according to the following procedure: 5 g of 1-oxo-6-methoxy-7,8-dichloro-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole were dissolved in a mixture of 77 ml of ethanol and 51 ml of water. 13.9 g of potassium hydroxide were added, and the solution was heated to refluxing temperature overnight under a nitrogen atmosphere. The reaction mixture was cooled, and the pH adjusted to about 4 by the addition of 12N aqueous hydrochloric acid. A precipitate formed in the acidic solution, which precipitate was isolated by filtration, and the filter cake washed with water. 5.15 g of 3-(2-aminoethyl)-5-methoxy-6,7-dichloroindol-2-carboxylic acid were obtained. The compound melted at 248°-249° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureto refluxing temperature overnight under a nitrogen atmosphere
  3. temperatureThe reaction mixture was cooled
  4. customA precipitate formed in the acidic solution
  5. customwhich precipitate was isolated by filtration
  6. washthe filter cake washed with water

Sources & evidence

ORD record
ord-e1aac02e290c4c3a879bd9abbb82a85e
Source dataset
uspto-grants-1986_09
Patent number
US04614807

Reaction notes

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