Chloral Hydrate → HCID 86740595, compound

HRID 1284918Notes

Reaction equation

HRID 1284918 reaction equation
Cl.[CH3:2][N:3]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[C:5](=[C:6]([NH2:19])[CH:7]=[CH:8][CH:9]=2)[CH2:4]1.Cl[C:21](Cl)(Cl)[CH:22]([OH:24])O.[O-]S([O-])(=O)=O.[Na+].[Na+].Cl.[NH2:35][OH:36].[OH-].[Na+]>O.CO>[CH3:2][N:3]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:10]2[C:5](=[C:6]([NH:19][C:22](=[O:24])[CH:21]=[N:35][OH:36])[CH:7]=[CH:8][CH:9]=2)[CH2:4]1

Participants

8

Reactant 5

HCID 2707Chloral HydrateHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 20250785HCID 20250785, compound

Product 1

HCID 86740595HCID 86740595, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
106 °C

Procedure

A solution of 10.75 g (0.0345 mol) of N-methyl-4-phenyl-8-amino-isoquinoline hydrochloride in 22 ml of H2O was added to 6.23 g (0.0376 mol) of chloral hydrate in 86 ml of water. After 5 minutes, 42.5 g of Na2SO4 and a solution of 7.6 g (0.109 mol) of hydroxylamine hydrochloride in 36 ml of H2O were added. The reaction mixture was warmed to 106° C. (internal temperature) in the course of 40 minutes. After 2 minutes, the mixture was cooled rapidly to 18° C. with ice/H2O. 200 ml of methanol were added to the reaction mixture and a pH of 7.6 was established with 2N NaOH. The precipitate which had separated out was filtered off with suction and washed thoroughly with H2O. After drying, 9.7 g (90.2% of theory) of crude product of melting point 151.3° C. (Mettler FP 61) were obtained.

Workup

  1. waitAfter 2 minutes
  2. customThe precipitate which had separated out
  3. filtrationwas filtered off with suction
  4. washwashed thoroughly with H2O
  5. customAfter drying
  6. custom9.7 g (90.2% of theory) of crude product of melting point 151.3° C. (Mettler FP 61) were obtained

Sources & evidence

ORD record
ord-df77ca2a6a624e44ad319f23246e88b6
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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