4-Methoxybenzylamine → HCID 178502533, compound

HRID 1498045Notes

Reaction equation

HRID 1498045 reaction equation
C(O[CH:4]=[N:5][NH:6][C:7]([O:9][CH3:10])=[O:8])C.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>C(O)C>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][CH:4]=[N:5][NH:6][C:7]([O:9][CH3:10])=[O:8])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 59296942Methyl 2-(ethoxymethylene)hydrazinecarboxylate

Product 1

HCID 178502533HCID 178502533, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2-(ethoxymethylene)hydrazinecarboxylate (prepared according to the method of N. Shao et al., Tetrahedron Lett. 2006, 47, 6743-6746; 5.00 g, 34.2 mmol) and 4-methoxybenzylamine (4.44 mL, 34.2 mmol) were dissolved in ethanol (20 mL), and the reaction was heated to 50° C. for 2 hours, then allowed to stir at room temperature for 18 hours. Filtration provided the product as a solid. Yield: 4.80 g, 20.2 mmol, 59%. 1H NMR (400 MHz, CD3OD) δ 3.69 (br s, 3H), 3.78 (s, 3H), 4.27 (br s, 2H), 6.80 and 7.62 (2 br s, 1H), 6.89 (br d, J=8.5 Hz, 2H), 7.19-7.28 (br m, 2H).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-4504beba813d4208be329091ad140618
Source dataset
uspto-grants-2015_12
Patent number
US09200000B2

Reaction notes

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