Hydrochloric Acid → HCID 54012237, compound

HRID 2286089Notes

Reaction equation

HRID 2286089 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1N)[C:9]([CH3:15])([CH3:14])[CH2:8][C:7]2([CH3:17])[CH3:16])=[O:3].N([O-])=O.[Na+].[ClH:22]>O.[Cu]Cl>[CH3:1][C:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Cl:22])[C:9]([CH3:15])([CH3:14])[CH2:8][C:7]2([CH3:17])[CH3:16])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23668193Sodium NitriteHCID 54310732HCID 54310732, compound

Product 1

HCID 54012237HCID 54012237, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Procedure

113.1 g of (6-amino-1,1,3,3-tetramethyl-5-indanyl) methyl ketone are suspended in 2260 ml of 20% hydrochloric acid and the suspension is cooled down to 0°-5° C. The cold mixture is treated dropwise within 10 minutes with a solution of 33.9 g of sodium nitrite in 115 ml of water and the resulting solution is stirred for 30 minutes. The cold solution is subsequently introduced dropwise over a period of 2 hours while stirring into a solution of 243.2 g of copper (I) chloride in 250 ml of water and 250 ml of concentrated hydrochloric acid, which is warmed to 40°-45° C. The mixture is then cooled down, introduced into ice-water and extracted three times with methylene chloride. The organic extract is washed with a sodium chloride solution, dried over sodium sulphate and freed from solvent under reduced pressure. The residue is purified by adsorption on silica gel using hexane/acetone (19:1) for the elution. The (6-chloro-1,1,3,3-tetramethyl-5-indanyl) methyl ketone obtained from the eluate melts at 69°-71° C. after recrystallisation from hexane/ether.

Workup

  1. temperaturethe suspension is cooled down to 0°-5° C
  2. additionThe cold solution is subsequently introduced dropwise over a period of 2 hours
  3. temperatureis warmed to 40°-45° C
  4. temperatureThe mixture is then cooled down
  5. extractionextracted three times with methylene chloride
  6. extractionThe organic extract
  7. washis washed with a sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. customThe residue is purified by adsorption on silica gel
  10. washfor the elution

Sources & evidence

ORD record
ord-1be0c19507f64d108854e19283d9611a
Source dataset
uspto-grants-1982_04
Patent number
US04326055

Reaction notes

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