Water → 2-(2,3-Dihydro-1H-imidazo[1,2-b]pyrazol-7-yl)ethanamine

HRID 349570Notes

Reaction equation

HRID 349570 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N+:7](/[CH:10]=[CH:11]/[C:12]1[CH:16]=[N:15][N:14]2[CH2:17][CH2:18][N:19](C=O)[C:13]=12)([O-])=O.[F-].[Na+].O>O1CCCC1>[NH:19]1[C:13]2[N:14]([N:15]=[CH:16][C:12]=2[CH2:11][CH2:10][NH2:7])[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 179619667-[(E)-2-nitroethenyl]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 1357327622-(2,3-Dihydro-1H-imidazo[1,2-b]pyrazol-7-yl)ethanamineYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (465 mg) in tetrahydrofuran (10 ml) was added 7-[(E)-2-nitroethenyl]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1-carbaldehyde (300 mg) under ice-cooling. The mixture was refluxed for 1.5 hours. After cooling on an ice bath, sodium fluoride (2.06 g) and water (0.882 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. The filtrate was concentrated in vacuo to give 2-(2,3-dihydro-1H-imidazo[1,2-b]pyrazol-7-yl)ethylamine (165 mg). This product was used in the next step without further purification.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 1.5 hours
  3. temperatureAfter cooling on an ice bath
  4. customThe insoluble materials were removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-10ad07b774bf4cf797356dd40d41a0f9
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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