Ammonia → HCID 85719099, compound

HRID 1418035Notes

Reaction equation

HRID 1418035 reaction equation
[S-:1][C:2]#[N:3].[NH4+].C(Cl)(=O)C1C=CC=CC=1.[CH3:14][C:15]1[C:16]([NH2:25])=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[N:20][CH:19]=[CH:18]2.N>CC(C)=O.C(O)C>[CH3:14][C:15]1[C:16]([NH:25][C:2]([NH2:3])=[S:1])=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[N:20][CH:19]=[CH:18]2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 397336986-Methylisoquinolin-5-amine2×

Product 1

HCID 85719099HCID 85719099, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 702EthanolSolvent

Procedure

1.7 g of ammonium thiocyanate are dissolved in 30 ml of acetone, 2.6 ml of benzoyl chloride are then added and the reaction mixture is heated at reflux for 15 minutes. 2.7 g of 6-methyl-5-isoquinolylamine (Compound 28), dissolved in 20 ml of acetone, are added. The reaction mixture is heated for 30 minutes and then evaporated to dryness. The residue is taken up in water and the remaining precipitate is filtered off. The compound thus obtained is deprotected with 10 ml of a 30% ammonia solution and 20 ml of ethanol at reflux for 2 hours. Evaporation is carried out to dryness and the residue is triturated in a 75/25 (v/v) ethyl acetate/hexane mixture, to obtain 3.5 g of a white powder. 1H NMR (CDCl3): 2.38 (s, 3H, --CH3), 3.36 (s, 2H, --NH2), 6.58 (s, 1H, --NH--), 7.47-7.60 (m, 2H, H7, H4), 7.98 (m, 1H, H8), 8.50 (m, 1H, H3), 9.26 (s, 1H, H1) .

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 15 minutes
  3. additionare added
  4. temperatureThe reaction mixture is heated for 30 minutes
  5. customevaporated to dryness
  6. filtrationthe remaining precipitate is filtered off
  7. customThe compound thus obtained
  8. temperatureat reflux for 2 hours
  9. customEvaporation
  10. customthe residue is triturated in a 75/25 (v/v) ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-dc779e1e259f4a39ba63f2b73d8cb717
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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