HCID 178462753, compound → HCID 178462457, compound

HRID 443477Notes

Reaction equation

HRID 443477 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH2:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:17][NH:18][C:19]([NH2:21])=[NH:20])[CH3:7].[CH2:22]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[CH2:33][NH:34][C:35]([NH2:37])=[NH:36])[CH3:23]>C(O)(=O)C.S(=O)(=O)(O)O.[Pd].S([O-])([O-])(=O)=O.[Ba+2]>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH2:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[CH2:17][NH:18][C:19]([NH2:21])=[NH:20])[CH3:7].[CH2:22]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH:25]1[CH2:33][NH:34][C:35]([NH2:37])=[NH:36])[CH3:23]

Participants

5

Reactant 1

HCID 178462753HCID 178462753, compound

Product 1

HCID 178462457HCID 178462457, compound

Reagents, catalysts & solvents 3

HCID 16218511Pd barium sulfateCatalystHCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 26.5 g of 1-ethyl-2-guanidinomethylindole hemisulphate (obtainable from ethyl indole-2-carboxylate via ethyl 1-ethyl-indole-2-carboxylate, 1-ethyl-2-hydroxymethyl-indole, 1-ethyl-2-chloromethyl-indole, 1-ethyl-2-phthalimidomethyl-indole and 1-ethyl-2-aminomethyl-indole) in a mixture of 300 ml of acetic acid and 70 ml of 2 N sulphuric acid is hydrogenated at 60° C. with 10 g of palladium/barium sulphate (5%) under normal pressure. After the absorption of hydrogen has ceased, the solution is filtered. The filtrate is evaporated and 1-ethyl-2-guanidinomethylindoline hemisulphate is obtained, m.p. 199° C.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe solution is filtered
  3. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-8129997899e441f3b412c15ecd96863e
Source dataset
uspto-grants-1981_04
Patent number
US04260628

Reaction notes

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