Potassio isocyanate → N-(4,4-Dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-7-yl)urea

HRID 621416Notes

Reaction equation

HRID 621416 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])([CH3:14])[C:7](=[O:13])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[N-:16]=[C:17]=[O:18].[K+]>C(O)(=O)C>[CH3:14][C:6]1([CH3:15])[C:5]2[C:10](=[CH:11][C:2]([NH:1][C:17]([NH2:16])=[O:18])=[CH:3][CH:4]=2)[C:9](=[O:12])[NH:8][C:7]1=[O:13]

Participants

4

Reactant 2

HCID 11051572Potassio isocyanateHCID 135581517-amino-4,4-dimethylisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 21242858N-(4,4-Dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-7-yl)urea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.3 g. (6.3 mMole) 7-amino-4,4-dimethylisoquinoline-1,3-dione was suspended in 30 ml. 2N acetic acid, mixed with 1.0 g. (12.5 mMole) potassium isocyanate and stirred for 6 hours at 80° C. The reaction mixture was cooled and the precipitate was filtered off with suction and washed with water. The residue was dissolved in dilute aqueous sodium hydroxide solution, the solution was neutralised with dilute hydrochloric acid, the residue was filtered off with suction and, for purification, worked up with ethanol and filtered off with suction. Yield: 0.6 g. (38.5% of theory); m.p. 260°-264° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed with water
  4. dissolutionThe residue was dissolved in dilute aqueous sodium hydroxide solution
  5. filtrationthe residue was filtered off with suction and, for purification
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-e606f20b4a8b483aa06baaab95ff68a3
Source dataset
uspto-grants-1989_04
Patent number
US04824835

Reaction notes

Loading…