Cyanamide → 3-Amidino-1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b]quinoline

HRID 1288203Notes

Reaction equation

HRID 1288203 reaction equation
[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:3]=12.[N:17]#[C:18][NH2:19]>C(O)(=O)C.C(O)C>[C:18]([N:14]1[CH2:15][CH2:16][C:3]2[C:4](=[N:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[CH3:1])[CH2:12][CH2:13]1)(=[NH:17])[NH2:19]

Participants

5

Reactant 2

HCID 9864CyanamideHCID 304399911-methyl-2,3,4,5-tetrahydro-1H-azepino[4,5-b]quinoline

Product 1

HCID 215034273-Amidino-1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b]quinoline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

5 gm (23.6 millimols) of 1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b]quinoline were dissolved in 2.7 ml of glacial acetic acid and 20 ml of ethanol, and the solution was stirred at room temperature with 1.12 gm (26.6 millimols) of cyanamide for 72 hours. Thereafter, the product which had crystallized out was dissolved in water and reprecipitated with sodium hydroxide. Yield: 0.6 gm, 10% of theory; m.p. 140° C.

Workup

  1. customThereafter, the product which had crystallized out
  2. dissolutionwas dissolved in water
  3. customreprecipitated with sodium hydroxide

Sources & evidence

ORD record
ord-3cf696a0718f48b8a1d830c2f69879d5
Source dataset
uspto-grants-1976_10
Patent number
US03987047

Reaction notes

Loading…