tert-butyl N-(2-hydroxyethyl)carbamate → 4-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrile

HRID 872551Notes

Reaction equation

HRID 872551 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2].O[CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C>>[NH2:20][CH2:19][CH2:18][N:15]1[CH:14]=[CH:13][C:12]([C:10]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=2)=[N:16]1

Participants

3

Reactant 2

HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 671687892-nitro-4-(1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 671725774-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrileYield 63.6%

Procedure

The title compound was prepared from 2-nitro-4-(1H-pyrazol-5-yl)benzonitrile (0.828 g, 3.87 mmol) and tert-butyl 2-hydroxyethylcarbamate (0.748 g, 4.64 mmol) using the method of Example 34(c) affording 0.633 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 3.21-3.29 (m, 2H), 4.02-4.04 (m, 2H), 7.02 (d, 1H), 7.88 (d, 1H), 8.13 (d, 1H), 8.29 (m, 1H), 8.50 (d, 1H).

Sources & evidence

ORD record
ord-fdce8d066c3848daac1917b57d0000d5
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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