Methanol → HCID 178497354, compound

HRID 1278724Notes

Reaction equation

HRID 1278724 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](C)=[C:4]([C:9]([OH:11])=[O:10])[C:3]=1N.Cl.CO[C:16](=[NH:29])[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.[CH3:30]O>>[CH3:30][O:11][C:9]([C:4]1[CH:5]=[CH:6][C:7]2[NH:29][C:16](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)=[N:1][C:2]=2[CH:3]=1)=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 184241152,3-Diamino-6-methylbenzoic acidHCID 86758495Methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride

Product 1

HCID 178497354HCID 178497354, compoundYield 56%

Procedure

A mixture of 1,2-diamino-4-methylcarboxybenzene (3.6 g; 20 mmol) and methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride (5.4 g; 20 mmol) in methanol (150 mL) was stirred at ambient temperature for 48 hours. Solution was concentrated to dryness. The residue was recrystallized from MeOH to obtain 3.8 g (56% yield) of the title compound as yellow solid, m.p. 185-188° C. Anal. Calcd. for C19H18N2O4: C, 67.45, H, 5.36; N, 8.28. Found: C, 67.25; H, 5.45; N, 8.28. Mass Spectrum: (EI; M+) m/z 338. 1H-NMR (DMSO-d6; 400 MHz) δ12.9 (broad s, 1H), 8.1 (s, 1H), 7.63-7.69 (d, 1H), 7.57-7.62 (d, 1H), 7.33 (d, 1H), 7.17-7.21 (dd 1H), 7.14-7.19 (d, 1H), 7.08-7.12 (d, 1H), 3.86 (s, 3H), 3.84 (s, 3H), 3.79 ppm (s, 3H)

Workup

  1. concentrationSolution was concentrated to dryness
  2. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-31afcb5ebbfc4916ac13451a42df3064
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

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