4-Methoxybenzene-1,2-diamine dihydrochloride → HCID 178488066, compound

HRID 1278721Notes

Reaction equation

HRID 1278721 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH2:12])[CH:6]=1.Cl.CO[C:16](=N)[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1.O.Cl>CO>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([CH:18]=[CH:17][C:16]2[NH:11][C:8]3[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][C:7]=3[N:12]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 30851614-Methoxybenzene-1,2-diamine dihydrochlorideHCID 21885828Hydrate;hydrochlorideHCID 86758495Methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride

Product 1

HCID 178488066HCID 178488066, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-methoxy-1,2-phenylenediamine dihydrochloride (1.55 g; 7.3 mmol) and methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride (1.9 g; 7.3 mmol) in methanol (50 mL) was stirred at ambient temperature for 72 hours. The methanol was concentrated to 25 mL. A yellow solid was separated by filtration. The solid was suspended in MeOH (10 mL), and treated with hydrogen chloride. The precipitate that formed was collected to obtain 515 mg (21% yield) of the title compound as a mono-hydrochloride, hydrate, yellow solid, m.p. 246-249° C. Anal. Calcd. for C18H18N2O3HCl. H2O: C, 61.72, H, 5.20; N, 7.79. Found: C, 61.61; H, 5.37; N, 7.84 . Mass spectrum: (EI; M+) m/z 310. 1H-NMR (DMSO-d6; 400 MHz) δ14.8 (broad s,1H), 8.3-8.5(d,1H), 7.62-7.63 (d, 1H), 7.3 (d,1H), 7.21-7.23 (dd 1H), 7.2 (d, 2H), 7.07-7.16(m, 3H), 3.86-3.88 (d, 6H), 3.82-3.84 ppm (s, 3H).

Workup

  1. concentrationThe methanol was concentrated to 25 mL
  2. customA yellow solid was separated by filtration
  3. additiontreated with hydrogen chloride
  4. customThe precipitate that formed
  5. customwas collected

Sources & evidence

ORD record
ord-0052372e518c431cb91ab11649fa75b4
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

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