Water → HCID 19420928, compound

HRID 864055Notes

Reaction equation

HRID 864055 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2C([C:6](=[CH2:13])[CH:7](O)[C:8]2=O)=CC=1.[NH:14]([CH2:16][CH:17](O)[CH3:18])[NH2:15].[OH2:20].[C:21]1(C)[CH:26]=CC=C[CH:22]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]1[CH:10]=[CH:9][CH2:8][C:7]2[C:18]=1[CH:17]=[C:16]1[C:6]=2[CH:13]=[N:15][N:14]1[CH2:22][CH:21]([OH:20])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 2361671-Hydrazinylpropan-2-olHCID 19420936HCID 19420936, compound

Product 1

HCID 19420928HCID 19420928, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A solution of 1.42 g (8.0 mmol) of 6-fluoro-2-hydroxy-methylene-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 1.5 hours. After concentration in a vacuum, the reaction mixture was purified by column chromatography on silica gel (ethyl acetate). 1.5 g (81%) of (RS)-1-(7-fluoro-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol were obtained as a yellow solid 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)

Sources & evidence

ORD record
ord-5d87cf80ace347a8ba00f8edb2cbe880
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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