Hydrochloric Acid → HCID 178429129, compound

HRID 67261Notes

Reaction equation

HRID 67261 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl.[N:11]([O-])=O.[Na+].[OH:15][C:16]1[CH:21]=[C:20]([CH3:22])[O:19][C:18](=[O:23])[CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][N:11]=[C:17]2[C:16](=[O:15])[CH:21]=[C:20]([CH3:22])[O:19][C:18]2=[O:23])=[CH:3][CH:4]=1)#[N:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 133964-AminobenzonitrileHCID 23668193Sodium NitriteHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 178429129HCID 178429129, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
5 °C

Procedure

To a mixture of 5.9 g (0.05 mol) 4-aminobenzonitrile and 20 ml of 12 N hydrochloric acid in 25 ml of water, cooled to 5° C., there is added dropwise a solution of 3.8 g (0.055 mol) sodium nitrite in 10 ml of water. The solution formed is added to an ice cooled solution of 6.3 g (0.05 mol) 4-hydroxy-6-methyl pyr-2-one and 22 g (0.205 ml) of sodium carbonate in 125 ml of water. The suspension formed is stirred at 5° C. for 1 hr., at room temperature for 3 hrs. and is vacuum filtered. The filter cake is air dried to afford 12 g (94% yield) of product, mp 300° C.

Workup

  1. customThe solution formed
  2. customThe suspension formed
  3. wait, at room temperature for 3 hrs
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-236093d98fb14bc38167b58ce71c6dc3
Source dataset
uspto-grants-1982_08
Patent number
US04345934

Reaction notes

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