Water → N-(5-Hydroxy-2-oxo-1,2,3,4-tetrahydroquinolin-8-yl)urea

HRID 26029Notes

Reaction equation

HRID 26029 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([OH:14])=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[C-:15]#[N:16].[K+].[OH2:18]>>[OH:14][C:6]1[CH:5]=[CH:4][C:3]([NH:2][C:15]([NH2:16])=[O:18])=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:13])[NH:11]2

Participants

4

Reactant 3

HCID 962Water2×HCID 9032Potassium CyanideHCID 213263748-Amino-5-hydroxy-3,4-dihydrocarbostyril hydrochloride

Product 1

HCID 21326284N-(5-Hydroxy-2-oxo-1,2,3,4-tetrahydroquinolin-8-yl)urea

Conditions

Temperature
50 °C

Procedure

10.7 g of 8-amino-5-hydroxy-3,4-dihydrocarbostyril hydrochloride was dissolved in 300 ml of water, and a solution of 4.06 g of potassium cyanide dissolved in 100 ml of water was added thereto while stirring at a temperature of 50° C. After stirring the mixture for one hour at 50° C., the precipitated crystals were recovered by filtration, washed successively with 1 l of water and methanol to obtain 8.75 g of 5-hydroxy-8-ureido-3,4-dihydrocarbostyril as colorless amorphous crystals having a melting point of 209.0°-211.2° C.

Workup

  1. additionwas added
  2. stirringAfter stirring the mixture for one hour at 50° C.
  3. filtrationthe precipitated crystals were recovered by filtration
  4. washwashed successively with 1 l of water and methanol

Sources & evidence

ORD record
ord-32a5ec3942d1470fa6debb2d4035ff21
Source dataset
uspto-grants-1979_04
Patent number
US04147869

Reaction notes

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