Phenylacetone → HCID 70381759, compound

HRID 2352084Notes

Reaction equation

HRID 2352084 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:14]1([CH2:20][C:21](=O)[CH3:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:12][C:6]1([CH3:13])[C:7](=[O:11])[NH:8][C:9]2[CH:10]=[C:2]3[C:3](=[CH:4][C:5]1=2)[C:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:21]([CH3:22])[NH:1]3

Participants

4

Reactant 2

HCID 7678PhenylacetoneHCID 135892296-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 70381759HCID 70381759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Analogously to Example 5, 4 g. (22.7 mmole) 6-amino-3,3-dimethylindolin-2-one are diazotised and reduced. Subsequently, 3 g. (22.3 mole) phenylacetone are added thereto and the reaction mixture further stirred for 18 hours at 25° C. The oil which separates out is shaken out several times with methylene chloride, evaporated and the residue worked up with cyclohexane and filtered off with suction. The solid residue is again dissolved in methylene chloride, washed twice with aqueous sodium hydrogen carbonate solution and once with water, dried with anhydrous sodium sulphate with the addition of charcoal and crystallised from methylene chloride. Yield 1.25 g. (19% of theory); m.p. 233°-235° C.

Workup

  1. customevaporated
  2. filtrationfiltered off with suction
  3. dissolutionThe solid residue is again dissolved in methylene chloride
  4. washwashed twice with aqueous sodium hydrogen carbonate solution and once with water
  5. dry with materialdried with anhydrous sodium sulphate with the addition of charcoal
  6. customcrystallised from methylene chloride

Sources & evidence

ORD record
ord-c0926ab0f33e4b1bb06b025fff758b6c
Source dataset
uspto-grants-1989_10
Patent number
US04874756

Reaction notes

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