Hydrochloric Acid → HCID 13093615, compound

HRID 1762934Notes

Reaction equation

HRID 1762934 reaction equation
[ClH:1].[C:2]([NH:6][CH2:7][C:8]#N)([CH3:5])([CH3:4])[CH3:3].[CH2:10]([O:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[OH:26])=[O:16])[CH2:11][CH2:12][CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].Cl.[N+](C1C=CC=CC=1)([O-])=[O:33]>>[ClH:1].[CH2:10]([O:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([C:8](=[O:33])[CH2:7][NH:6][C:2]([CH3:3])([CH3:4])[CH3:5])[CH:22]=[CH:21][C:20]=2[OH:26])=[O:16])[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7416NitrobenzeneHCID 6451240Aluminum(III) ChlorideHCID 13093609Butyl 7-hydroxy-1H-indole-2-carboxylateHCID 13416931HCID 13416931, compound

Product 1

HCID 13093615HCID 13093615, compound

Procedure

Under ice cooling and agitation, 818 mg of tert-butylaminoacetonitrile hydrochloride and 1.2 g of 7-hydroxyindole-2-carboxylic acid n-butyl ester are added to a solution of 2.7 g of aluminum chloride in 20 ml of nitrobenzene. Then gaseous hydrogen chloride is introduced into the mixture at 0° to 3° C. for 7 hours, the reaction mixture is stirred for 16 hours at 0°-3° C., and then poured into ice water. The mixture is agitated for 10 minutes and then the precipitate is vacuum-filtered. The precipitate is recrystallized from isopropanol, thus obtaining 765 mg of 4-tert-butylaminoacetyl-7-hydroxyindole-2-carboxylic acid n-butyl ester hydrochloride, decomposition point 203°-208° C.

Workup

  1. stirringThe mixture is agitated for 10 minutes
  2. filtrationthe precipitate is vacuum-filtered
  3. customThe precipitate is recrystallized from isopropanol

Sources & evidence

ORD record
ord-fd4aac5143a94cd3a4d6ac8afb264683
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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