Water → 5-amino-4-(2-aminoethyl)-1-(2-triphenylmethyloxyethyl)-1H-pyrazole

HRID 349550Notes

Reaction equation

HRID 349550 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[N:12]([CH2:13][CH2:14][O:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:11]=[CH:10][C:9]=1/[CH:35]=[CH:36]/[N+:37]([O-])=O.[F-].[Na+].O>O1CCCC1>[NH2:7][C:8]1[N:12]([CH2:13][CH2:14][O:15][C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:11]=[CH:10][C:9]=1[CH2:35][CH2:36][NH2:37]

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 179619895-amino-4-[(E)-2-nitroethenyl]-1-(2-triphenylmethyloxyethyl)-1H-pyrazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 179619655-amino-4-(2-aminoethyl)-1-(2-triphenylmethyloxyethyl)-1H-pyrazoleYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (3.22 g) in tetrahydrofuran (100 ml) was added 5-amino-4-[(E)-2-nitroethenyl]-1-(2-triphenylmethyloxyethyl)-1H-pyrazole (4.4 g) under ice-cooling. The mixture was refluxed for 5 hours. After cooling on an ice bath, sodium fluoride (14.3 g) and water (6.12 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. The filtrate was concentrated in vacuo to give 5-amino-4-(2-aminoethyl)-1-(2-triphenylmethyloxyethyl)-1H-pyrazole (3.63 g). This product was used in the next step without further purification.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 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-f01b71e726264165b778faec246c47c5
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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