Nitromethane → 5-amino-4-[(E)-2-nitroethenyl]-1-(2-triphenylmethyloxyethyl)-1H-pyrazole

HRID 349549Notes

Reaction equation

HRID 349549 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][O:9][C:10]([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)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][C:3]=1[CH:29]=O.C([O-])(=O)C.[NH4+].[N+:36]([CH3:39])([O-:38])=[O:37]>>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][O:9][C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][C:3]=1/[CH:29]=[CH:39]/[N+:36]([O-:38])=[O:37]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 179619611-(2-Triphenylmethyloxyethyl)-5-aminopyrazole-4-carbaldehyde

Product 1

HCID 179619895-amino-4-[(E)-2-nitroethenyl]-1-(2-triphenylmethyloxyethyl)-1H-pyrazole

Procedure

A solution of 5-amino-1-(2-triphenylmethyloxyethyl)-1H-pyrazole-4-carbaldehyde (15 g) and ammonium acetate (4.07 g) in nitromethane (300 ml) was refluxed for 6.5 hours. The reaction mixture was evaporated under reduced pressure and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give 5-amino-4—[(E)-2-nitroethenyl]-1-(2-triphenylmethyloxyethyl)-1H-pyrazole (4.46 g). 1H-NMR(DMSO-d6) δ3.15 (2H, t, J=4.9 Hz), 4.16 (2H, t, J=4.9 Hz), 6.96 (2H, s), 7.1–7.3 (15H, m), 7.75 (1H, d, J=12.9 Hz), 7.83 (1H, s), 8.27 (1H, d, J=12.9 Hz)

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b2af628a1f954b03876060252fae11e7
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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