Aluminium lithium hydride → HCID 11681118, compound

HRID 1170854Notes

Reaction equation

HRID 1170854 reaction equation
[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][CH2:12][C:11](=[CH:16][C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=O)[C:10]=3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].N1(CC=C2CCCC3N(C4C=CC=CC=4)N=CC2=3)CCOCC1>C1COCC1>[N:19]1([CH2:17]/[CH:16]=[C:11]2/[C:10]3[CH:9]=[N:8][N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:15]=3[CH2:14][CH2:13][CH2:12]/2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 66855576HCID 66855576, compoundHCID 66855611HCID 66855611, compound

Product 1

HCID 11681118HCID 11681118, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

An E/Z mixture of 4-(2-(1-phenyl-6,7-dihydro-1H-indazol-4(5H)-ylidene)acetyl)-morpholine (398 mg, 1.23 mmol) is added to a mixture of LiAlH4 (129 mg, 3.70 mmol) in THF (10 mL) cooled to 0° C. The temperature of the reaction is allowed to increase up to room temperature and is stirred for 4 hours, and then the reaction is refluxed for 30 minutes. The mixture is cooled in an ice bath and ice is added. The insoluble solid is filtered and washed with AcOEt. The organic phase is washed with H2O, dried and evaporated under reduced pressure, giving an E/Z mixture of 4,5,6,7-tetrahydro-4-(2-(morpholin-4-yl)ethylidene)-1-phenyl-1H-indazol which is purified by means of silica gel chromatography giving (E)-4,5,6,7-tetrahydro-4-(2-(morpholin-4-yl)ethylidene)-1-phenyl-1H-indazole (118 mg, 0.38 mmol, 31%) and an E/Z mixture of 4,5,6,7-tetrahydro-4-(2-(morpholin-4-yl)ethylidene)-1-phenyl-1H-indazole (80.2 mg, 0.26 mmol, 21%). The 1H NMR spectrum (300 MHz, CDCl3) of (E)-4,5,6,7-tetrahydro-4-(2-(morpholin-4-yl)ethylidene)-1-phenyl-1H-indazole coincides with the one obtained according to Method A.

Workup

  1. temperatureto increase up to room temperature
  2. temperaturethe reaction is refluxed for 30 minutes
  3. temperatureThe mixture is cooled in an ice bath
  4. additionice is added
  5. filtrationThe insoluble solid is filtered
  6. washwashed with AcOEt
  7. washThe organic phase is washed with H2O
  8. customdried
  9. customevaporated under reduced pressure
  10. customgiving
  11. customis purified by means of silica gel chromatography

Sources & evidence

ORD record
ord-915261e848c643c897c072be66b4dac1
Source dataset
uspto-grants-2010_11
Patent number
US07829559B2

Reaction notes

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