Hydrazine → 2-Hydrazinyl-4-isopropyl-1,8-naphthyridine

HRID 2368685Notes

Reaction equation

HRID 2368685 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][NH2:16]>>[NH:15]([C:2]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[NH2:16]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 866692872-Chloro-4-isopropyl-1,8-naphthyridine

Product 1

HCID 670830372-Hydrazinyl-4-isopropyl-1,8-naphthyridineYield 92%

Procedure

A solution of chloro-4-isopropyl-1,8-naphthyridine (690 mg, 3.4 mmol) in NH2NH2 was reacted as outlined in Scheme 1 above to give the desired title compound (620 mg, 92%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=6.74 Hz, 6 H) 3.45-3.59 (m, 1 H) 6.70 (br. s., 1 H) 7.21 (dd, J=8.06, 4.54 Hz, 1 H) 8.19 (d, J=7.62 Hz, 1H) 8.79 (br. s., 1 H).

Sources & evidence

ORD record
ord-df54d732f319430f9e3f00f93a472e26
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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