Toluene → HCID 62241651, compound

HRID 526412Notes

Reaction equation

HRID 526412 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])=[O:7])=[CH:4][N:3]=1.[NH2:16][NH2:17].C1(C)C=CC=CC=1>C(O)(C)C>[NH:16]([C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])=[O:7])=[CH:4][N:3]=1)[NH2:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 9321Hydrazine2×HCID 43089866HCID 43089866, compound

Product 1

HCID 62241651HCID 62241651, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 6-chloro-N-(3-methoxypropyl)nicotinamide (6.6 g, 28.9 mmol) and hydrazine (4.53 mL, 144 mmol) in isopropanol (100 mL) was heated at 80° C. for 21 h. More hydrazine (3 mL) was added and heating continued at 80° C. for 24 h. The reaction was then concentrated in vacuo to give a tan oil which was reconcentrated from toluene to give the title compound as its hydrochloride salt as a white solid in quantitative yield. MS m/z 225 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.66-1.78 (m, 2H) 3.18-3.30 (m, 5H) 3.35 (t, J=6.3 Hz, 2H) 6.68 (d, J=8.8 Hz, 1H) 7.87 (dd, J=8.8, 2.3 Hz, 1H) 7.99 (br. s., 1H) 8.20 (t, J=5.6 Hz, 1H) 8.49 (dd, J=2.4, 0.6 Hz, 1H).

Workup

  1. temperatureheating
  2. concentrationThe reaction was then concentrated in vacuo
  3. customto give a tan oil which

Sources & evidence

ORD record
ord-17b7692993f84b168491a91e5096ae8f
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

Loading…