Water → HCID 19420942, compound

HRID 864052Notes

Reaction equation

HRID 864052 reaction equation
O[CH:2]=[C:3]1CC2[C:5](=CC(C)=CC=2)[C:4]1=O.[NH:14]([CH2:16][CH:17]([OH:19])[CH3:18])[NH2:15].O.[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:27][C:21]1[CH:26]=[CH:25][CH2:24][C:23]2[C:22]=1[CH:2]=[C:3]1[C:4]=2[CH:5]=[N:15][N:14]1[CH2:16][CH:17]([OH:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 2361671-Hydrazinylpropan-2-olHCID 70185153HCID 70185153, compound

Product 1

HCID 19420942HCID 19420942, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A solution of 1.4 g (8.04 mmol) of 2-hydroxymethylene-6-methyl-1-indanone, 0.87 g (9.65 mmol) of (RS)-1-hydrazino-2-propanol and 100 mg of p-toluenesulfonic acid in 100 ml of anhydrous toluene was heated on a water separator for 2 hours. After concentration in a vacuum, the reaction mixture was purified by column chromatography on silica gel (ethyl acetate/hexane 4:1). 1.7 g (93%) of (RS)-1-(7-methyl-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol were obtained as a yellow oil which was used directly in the next reaction.

Workup

  1. concentrationAfter concentration in a vacuum
  2. customthe reaction mixture was purified by column chromatography on silica gel (ethyl acetate/hexane 4:1)

Sources & evidence

ORD record
ord-b8a06c19fee743f89e737082fb955ac6
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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