Ammonia → HCID 178420886, compound

HRID 1597362Notes

Reaction equation

HRID 1597362 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH:12]([NH2:15])[CH2:13][NH2:14])=[CH:3][CH:2]=1.Cl.[CH2:17](OC=N)C.N>ClCCl>[NH:14]1[CH2:13][CH:12]([CH2:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)[N:15]=[CH:17]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 12578842Ethyl formimidate hydrochlorideHCID 234992063-Quinolin-4-yl-propane-1,2-diamine

Product 1

HCID 178420886HCID 178420886, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-Quinolin-4-yl-propane-1,2-diamine (0.080 g, 3.98 mmol) in 5 ml of dry dichloromethane, formimidic acid ethyl ester hydrochloride (0.174 g, 7.36 mmol) (Ohme, R. et al. Angew.Chem.Int.Engl.Ed. 1967, 6, 90.) was added. The reaction mixture was stirred overnight at room temperature. Aqueous ammonia (2 ml) was added to he reaction mixture and was partitioned between EtOAc (2×5 ml) and water. The organic layer was dried, filtered and concentrated to give 0.084 g (110%) of the product as a syrup.

Workup

  1. customwas partitioned between EtOAc (2×5 ml) and water
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a88b5003f71472181902154acd0962e
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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