Hydrochloric Acid → HCID 178510261, compound

HRID 1159481Notes

Reaction equation

HRID 1159481 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:9]([O-])=O.[Na+].[C:13]([CH:15]([CH2:21][C:22]([O:24]CC)=O)C(OCC)=O)#[N:14].[OH-].[Na+]>N1C=CC=CC=1.O>[C:13]([C:15]1[CH:21]=[C:22]([OH:24])[N:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:9]=1)#[N:14]

Participants

8

Reactant 5

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

Product 1

HCID 178510261HCID 178510261, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Conditions

Temperature
2.5 °C

Procedure

120 ml of water and 15 ml of 35% hydrochloric acid were added to 5.6 g (0.06 mole) of aniline to obtain a solution. The solution was ice-cooled to 0 to 5° C. Thereto was drop-wise added, with stirring, 24 ml of water in which 4.2 g (0.06 mole) of sodium nitrite had been dissolved, after which stirring was conducted for 1 hour. Then, this aqueous diazonium salt solution was dropwise added to 120 ml of a pyridine solution containing 10.2 g (0.06 mole) of diethyl α-cyanosuccinate, with stirring under ice-cooling. After the dropwise addition, the mixture was stirred for 1 hour under ice-cooling and successively for 1 hour at room temperature, to give rise to a reaction. After the reaction, 240 ml of a 2% aqueous sodium hydroxide solution was added, followed by stirring for 2 hours. Then, the reaction mixture was drop-wise added to 240 ml of 35% hydrochloric acid under ice-cooling. The resulting crystals were collected by filtration, washed with 10 ml of water, and dried in a hot-air drier, to obtain 8.4 g of crude, reddish brown crystals of title compound. The crude crystals were recrystallized from diethyl ether-petroleum ether and dried in a hot-air drier, to obtain 5.7 g (yield: 51.3%) of a title compound as light yellow crystals.

Workup

  1. customto obtain a solution
  2. additionadded
  3. stirringafter which stirring
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. additionAfter the dropwise addition
  7. stirringthe mixture was stirred for 1 hour under ice-
  8. temperaturecooling and successively for 1 hour at room temperature
  9. customto give rise
  10. customto a reaction
  11. additionwas added
  12. stirringby stirring for 2 hours
  13. temperaturecooling
  14. filtrationThe resulting crystals were collected by filtration
  15. washwashed with 10 ml of water
  16. customdried in a hot-air drier,
  17. customto obtain 8.4 g of crude

Sources & evidence

ORD record
ord-4fae33c7cf9447a1917a096af0c9e869
Source dataset
uspto-grants-2010_10
Patent number
US07812175B2

Reaction notes

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