Sulfuric Acid → HCID 54467755, compound

HRID 2286090Notes

Reaction equation

HRID 2286090 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[C:6]2[C:10](=[C:11](N)[C:12]=1[Cl:13])[C:9]([CH3:16])([CH3:15])[CH2:8][C:7]2([CH3:18])[CH3:17])=[O:3].S(=O)(=O)(O)[OH:20].N([O-])=O.[Na+]>O>[CH3:1][C:2]([C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([OH:20])[C:12]=1[Cl:13])[C:9]([CH3:16])([CH3:15])[CH2:8][C:7]2([CH3:18])[CH3:17])=[O:3]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 23668193Sodium NitriteHCID 54477266HCID 54477266, compound

Product 1

HCID 54467755HCID 54467755, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

21.1 g of (6-chloro-7-amino-1,1,3,3-tetramethyl-5-indanyl) methyl ketone are introduced into 48 ml of concentrated sulphuric acid and, after the warming to 50° C., the mixture is treated slowly with 140 ml of distilled water. After cooling down to 0°-5° C., there is introduced dropwise into the mixture over a period of 45 minutes a solution of 5.5 g of sodium nitrite in 20 ml of water. The resulting cold mixture is introduced dropwise while stirring over a period of 2 hours into a solution, held at 70° C., of 60 ml of water and 60 ml of concentrated sulphuric acid. The mixture is cooled, then introduced into ice-water and extracted three times with ether. The organic phase 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/ether (19:1) for the elution. The (6-chloro-7-hydroxy-1,1,3,3-tetramethyl-5-indanyl) methyl ketone obtained from the eluate melts at 78°-80° C. after recrystallisation from hexane/ether.

Workup

  1. temperatureAfter cooling down to 0°-5° C.
  2. additionThe resulting cold mixture is introduced dropwise
  3. temperatureThe mixture is cooled
  4. extractionextracted three times with ether
  5. washThe organic phase is washed with a sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customThe residue is purified by adsorption on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-fa3b01dac00d46ac91529463e985e4b7
Source dataset
uspto-grants-1982_04
Patent number
US04326055

Reaction notes

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