Hydrochloric Acid → HCID 11579946, compound

HRID 543051Notes

Reaction equation

HRID 543051 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([O:3]C)=[O:2].Cl.[N:13]([O-])=O.[Na+].[OH:17][C:18]1[CH:23]=[C:22]([CH3:24])[O:21][C:20](=[O:25])[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:1]([C:5]1[CH:11]=[CH:10][C:8]([N:9]2[C:22]([CH3:24])=[CH:23][C:18](=[O:17])[C:19]([C:20]([OH:21])=[O:25])=[N:13]2)=[CH:7][CH:6]=1)([OH:3])=[O:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 12082Methyl 4-aminobenzoateHCID 23668193Sodium NitriteHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 11579946HCID 11579946, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To an ice cooled suspension of 11.33 g (0.075 mol) 4-carbomethoxy aniline in 40 ml of water there is added 30 ml of 12N hydrochloric acid. The suspension is cooled to 0° C. and to it there is added 5.7 g (0.0825 mol) of sodium nitrite in 15 ml of water, dropwise. The solution formed is added to an ice cooled solution of 9.45 g (0.075 mol) 4-hydroxy-6-methyl pyr-2-one and 33 g (0.3075 mol) of sodium carbonate in 190 ml of water (considerable foaming is observed). The suspension is stirred at 5° C. for 1 hr., room temperature for 2 hrs. And refluxed for 1/2 hr. The solution formed is allowed to stand at room temperature for 18 hrs. and is extracted with 3 (200 ml) portions of methylene dichloride. The aqueous solution is acidified with 12N hydrochloric acid at 10° C. and the suspension formed is vacuum filtered. The filter cake is boiled in 300 ml of methanol and vacuum filtered hot. The filter cake is air dried to afford 13.1 g (64% yield) of product, mp 290° C. decomp.

Workup

  1. customThe solution formed
  2. wait, room temperature for 2 hrs
  3. temperatureAnd refluxed for 1/2 hr
  4. customThe solution formed
  5. waitto stand at room temperature for 18 hrs
  6. extractionand is extracted with 3 (200 ml) portions of methylene dichloride
  7. customis acidified with 12N hydrochloric acid at 10° C.
  8. customthe suspension formed
  9. filtrationfiltered
  10. filtrationvacuum filtered hot
  11. customdried

Sources & evidence

ORD record
ord-dbb7b78501b14b55a80090bbd9dc83e1
Source dataset
uspto-grants-1987_04
Patent number
US04661145

Reaction notes

Loading…