Water → HCID 19420922, compound

HRID 864062Notes

Reaction equation

HRID 864062 reaction equation
OC=[C:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[CH:9]=2)[C:4]1=O.[NH:15]([CH2:17][CH:18]([OH:20])[CH3:19])[NH2:16].O.[C:22]1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5]([CH2:6][CH:7]=1)=[C:4]1[C:3]([N:15]([CH2:17][CH:18]([OH:20])[CH3:19])[N:16]=[CH:22]1)=[CH:11]2

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 2361671-Hydrazinylpropan-2-olHCID 69754267HCID 69754267, compound

Product 1

HCID 19420922HCID 19420922, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A solution of 1.4 g (7.36 mmol) of 2-hydroxymethylene-5-methoxy-1-indanone, 0.8 g (8.83 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 1.5 hours. After concentration in a vacuum, the reaction mixture was purified by column chromatography on silica gel (ethyl acetate/hexane 4:1). 1.74 g (97%) of (RS)-1-(6-methoxy-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-dbd5d448ccd14d87bd088f4e6f4b5909
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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