Hydrochloric Acid → HCID 178510261, compound

HRID 1725109Notes

Reaction equation

HRID 1725109 reaction equation
Cl.NC1C=CC=CC=1.N([O-])=O.[Na+].[Cl-].[C:14]1([N+:20]#[N:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:22]([CH:24]([CH2:30][C:31](OCC)=[O:32])C(OCC)=O)#[N:23].[OH-].[Na+]>N1C=CC=CC=1.O>[C:22]([C:24]1[CH:30]=[C:31]([OH:32])[N:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:21]=1)#[N:23]

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 6115AnilineHCID 14798Sodium HydroxideHCID 60992Benzenediazonium chlorideHCID 254669diethyl 2-cyanosuccinateHCID 23668193Sodium Nitrite

Product 1

HCID 178510261HCID 178510261, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Conditions

Temperature
2.5 °C

Procedure

Water (120 mL) and 15 mL of 35% hydrochloric acid were added to 5.6 g (0.06 mol) of aniline, and the mixture was dissolved. Subsequently, 24 mL of water having dissolved therein 4.2 g (0.06 mol) of sodium nitrite was added dropwise thereto with stirring under ice cooling to 0 to 5° C., and the resulting solution was stirred for 1 hour to prepare benzenediazonium chloride. An aqueous solution of this diazonium salt was added dropwise to a 120 mL pyridine solution containing 10.2 g (0.06 mol) of diethyl α-cyanosuccinate with stirring under ice cooling. After the dropwise addition, the solution was stirred under ice cooling for 1 hour and then at room temperature for 1 hour. When the reaction was completed, 240 mL of an aqueous 2% sodium hydroxide solution was added, followed by stirring for 2 hours. The obtained reaction solution was added dropwise to 240 mL of 35% hydrochloric acid under ice cooling, and the precipitated crystal was collected by filtration, washed with 10 mL of water and dried by a hot air drier to obtain 8.4 g of the crude crystal of the title compound as a red-brown crystal. This crude crystal was recrystallized from diethyl ether-petroleum ether and dried by a hot air drier to obtain 5.7 g (yield: 51.3%) of the title compound as a pale yellow crystal.

Workup

  1. dissolutionthe mixture was dissolved
  2. stirringthe resulting solution was stirred for 1 hour
  3. stirringwith stirring under ice cooling
  4. additionAfter the dropwise addition
  5. stirringthe solution was stirred under ice cooling for 1 hour
  6. stirringby stirring for 2 hours
  7. customThe obtained reaction solution
  8. filtrationthe precipitated crystal was collected by filtration
  9. washwashed with 10 mL of water
  10. customdried by a hot air drier
  11. customto obtain 8.4 g of the crude crystal of the title compound as a red-brown crystal
  12. customThis crude crystal was recrystallized from diethyl ether-petroleum ether
  13. customdried by a hot air drier

Sources & evidence

ORD record
ord-11edf75f72de4ba3963ac17d7c734fe7
Source dataset
uspto-grants-2009_02
Patent number
US07488831B2

Reaction notes

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