HCID 70062383, compound → HCID 86739497, compound

HRID 371438Notes

Reaction equation

HRID 371438 reaction equation
S([S:11]([OH:14])(=[O:13])=[O:12])(C1C=CC(C)=CC=1)(=O)=O.[N+:15]([C:18]1[CH:41]=[CH:40][C:21]([CH:22]=[CH:23][C:24]([O:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:37](=[NH:39])[NH2:38])[CH:33]=3)[CH:28]=2)=[O:25])=[CH:20][CH:19]=1)([O-])=O>C(O)(=O)C.[Zn]>[CH3:18][S:11]([OH:14])(=[O:13])=[O:12].[CH3:18][S:11]([OH:14])(=[O:13])=[O:12].[NH2:15][C:18]1[CH:19]=[CH:20][C:21]([CH:22]=[CH:23][C:24]([O:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:37](=[NH:38])[NH2:39])[CH:33]=3)[CH:28]=2)=[O:25])=[CH:40][CH:41]=1

Participants

4

Reactant 1

HCID 70062383HCID 70062383, compound

Product 1

HCID 86739497HCID 86739497, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

In 60 ml of acetic acid, was suspended 3 g of 6-amidino-2-naphthyl 4-nitrocinnamate tosylsulfonate. To the suspension, while being cooled in ice and stirred, was added 1.8 g of zinc dust. The mixture was stirred for 24 hours and removed of insolubles by filtration. The filtrate was neutralized, admixed with a saturated aqueous sodium hydrogencarbonate solution and the precipitate was suspended in methanol and admixed with methanesulfonic acid to dissolve the precipitate. Ethyl ether was added to the solution and the resulting oily substance was left standing at room temperature to solidify. Upon recrystallization from a methano-ethyl ether mixture, there was obtained 0.14 g of 6-amidino-2-naphthyl 4-aminocinnamate dimethanesulfonate.

Workup

  1. temperatureTo the suspension, while being cooled in ice
  2. stirringThe mixture was stirred for 24 hours
  3. customremoved of insolubles by filtration
  4. dissolutionto dissolve the precipitate
  5. additionEthyl ether was added to the solution
  6. waitthe resulting oily substance was left
  7. customstanding at room temperature
  8. customUpon recrystallization from a methano-ethyl ether mixture

Sources & evidence

ORD record
ord-d0e7d035740e457b99ac17ac8fc45835
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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