Ethanol → HCID 67596793, compound

HRID 581700Notes

Reaction equation

HRID 581700 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:23]C1C=C2C(CCC2=NO)=CC=1.[Na].C(O)C>C1(C)C=CC=CC=1>[ClH:23].[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([Cl:23])=[CH:7][CH:8]=2)[C:3]1=[O:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 4145312-Amino-2,3-dihydro-1H-inden-1-oneHCID 5360545SodiumHCID 86754188HCID 86754188, compound

Product 1

HCID 67596793HCID 67596793, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Amino-6-chloro-1-indanone hydrochloride is prepared in the same way as in Example 1 for the preparation of 2-amino-1-indanone, starting from 57.5 g of 6-chloro-1-indanone oxime p-toluenesulphonate, 3.94 g of sodium, 200 ml of absolute ethanol and 1 litre of anhydrous toluene. After 15 hours of reaction at 0° C., the precipitate formed is filtered off on Celite, the filtrate washed with water and then extracted with IN hydrochloric acid (2×500 ml) and the aqueous phase concentrated to dryness under reduced pressure. 10.5 g of expected product are obtained in the form of a brown-green solid, the melting point of which is above 260° C.

Workup

  1. customAfter 15 hours of reaction at 0° C.
  2. customthe precipitate formed
  3. filtrationis filtered off on Celite
  4. washthe filtrate washed with water
  5. extractionextracted with IN hydrochloric acid (2×500 ml)
  6. concentrationthe aqueous phase concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-24925a6c0e5649589f0df39f7b2822c1
Source dataset
uspto-grants-1999_07
Patent number
US05922716

Reaction notes

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