Hydrochloric Acid → HCID 21929625, compound

HRID 1243840Notes

Reaction equation

HRID 1243840 reaction equation
[C:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:11][C:10]=3[N:9](COCC[Si](C)(C)C)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2C3C=CC(C4C=CC=CC=4)(C4C=CC=CC=4)CC=3NN2COCC[Si](C)(C)C)C=CC=CC=1.Cl>C(O)C.O>[C:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:11][C:10]=3[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21928822HCID 21928822, compoundHCID 21929476HCID 21929476, compound

Product 1

HCID 21929625HCID 21929625, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 0.16 g of 3,6,6-triphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole and 3,6,6-triphenyl-2-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazole is dissolved in 3.4 cm3 of ethanol and 1 cm3 of water, and 3.4 cm3 of an approximately 2N ethanolic solution of hydrogen chloride are then added. The solution is stirred for about 4 hours at a temperature in the region of 65° C. The reaction mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 50 cm3 of water, and the pH is brought to about 10 by addition of aqueous 0.1N sodium hydroxide solution. After extraction with three times 50 cm3 of ethyl acetate, the combined organic phases are washed with 50 cm3 of aqueous 0.1N sodium hydroxide solution, 50 cm3 of water and 50 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). After flash chromatography on a column of silica [eluent: dichloromethane], 0.06 g of 3,6,6-triphenyl-6,7-dihydro-1H-indazole is thus obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (13 kPa)
  2. additionthe pH is brought to about 10 by addition of aqueous 0.1N sodium hydroxide solution
  3. extractionAfter extraction with three times 50 cm3 of ethyl acetate
  4. washthe combined organic phases are washed with 50 cm3 of aqueous 0.1N sodium hydroxide solution, 50 cm3 of water and 50 cm3 of saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-e6210ad021ca40a2b0be8936956c0ba6
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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