Hydrochloric Acid → HCID 20544734, compound

HRID 1660034Notes

Reaction equation

HRID 1660034 reaction equation
[ClH:1].N[C:3]1[CH:12]=[CH:11][C:6]2[O:7][CH2:8][CH2:9][O:10][C:5]=2[C:4]=1[C:13]([OH:15])=[O:14].Cl.N([O-])=O.[Na+]>O>[Cl:1][C:3]1[CH:12]=[CH:11][C:6]2[O:7][CH2:8][CH2:9][O:10][C:5]=2[C:4]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23668193Sodium NitriteHCID 70548312HCID 70548312, compound

Product 1

HCID 20544734HCID 20544734, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

58 g of 6-amino-1,4-benzodioxane-5-carboxylic acid hydrochloride and 116 ml of water were introduced in a 500 ml balloon flask provided with a stirrer, a thermometer and a dropping funnel. 28 ml of hydrochloric acid (d=1.18) were added and the mixture was cooled to a temperature of from 0°-5° C. A solution of 17.5 g of sodium nitrite in 38 ml of water was added at a temperature within the 0°-5° C. range. The mixture was stirred for one hour. 20 g of cuprous chloride and 75 ml of hydrochloric acid were added. The mixture was allowed to stand overnight and then filtered. The solid was washed with water, dried at 50° C. and purified by treatment with carbon black in alkaline solution (200 ml of water and 25 ml of 36° Be' caustic soda lye) and then 25 ml of hydrochloric acid was added. 40 g of 6 -chloro-1,4-benzodioxane-5-carboxylic acid were obtained (M.P. 162° C.; yield: 74%).

Workup

  1. customprovided with a stirrer
  2. temperaturethe mixture was cooled to a temperature of from 0°-5° C
  3. waitto stand overnight
  4. filtrationfiltered
  5. washThe solid was washed with water
  6. customdried at 50° C.
  7. custompurified by treatment with carbon black in alkaline solution (200 ml of water and 25 ml of 36° Be' caustic soda lye)
  8. addition25 ml of hydrochloric acid was added

Sources & evidence

ORD record
ord-a9b3e535534741348b6adb2adfd58d7a
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Reaction notes

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