Hydrochloric Acid → HCID 21286381, compound

HRID 2231215Notes

Reaction equation

HRID 2231215 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[CH2:16][CH:15]3[C:10]([C:11]4[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:12]=4[CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[C-:35]#[N:36].[K+]>O>[Cl:23][C:21]1[CH:20]=[CH:19][C:12]2[CH2:13][CH2:14][CH:15]3[C:10]([C:11]=2[CH:22]=1)=[N:9][N:8]([C:5]1[CH:6]=[CH:7][C:2]([C:35]#[N:36])=[CH:3][CH:4]=1)[C:17](=[O:18])[CH2:16]3

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 212863822-(4-aminophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-oneHCID 23668193Sodium Nitrite

Product 1

HCID 21286381HCID 21286381, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-Aminophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one is added to the mixture of water and concentrated hydrochloric acid which is cooled on an ice bath and then an aqueous solution of sodium nitrite is added dropwise. The mixture is stirred under ice-cooling for 30 minutes and then neutralized with sodium carbonate. The solution is added dropwise with stirring to a solution of cuprous cyanide and potassium cyanide which is previously prepared. The mixture is stirred under ice-cooling for 30 minutes and allowed to stand overnight at room temperature. The precipitated crystals are collected by filtration to give 9-chloro-2-(4-cyanophenyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.

Workup

  1. temperatureis cooled on an ice bath
  2. temperaturecooling for 30 minutes
  3. additionThe solution is added dropwise
  4. customis previously prepared
  5. stirringThe mixture is stirred under ice-
  6. temperaturecooling for 30 minutes
  7. filtrationThe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-c1a7bb02900443f19c268a61d20b9f3b
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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