Benzylamine → 2-amino-N-benzyl-6-methoxybenzamide

HRID 400315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400315
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=O.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C.[Cl-].ClC1N(C)CC[NH+]1C>ClCCl.O>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:6]

Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 27353572-Amino-6-methoxybenzoic AcidHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride

Produkt 1

HCID 583841432-amino-N-benzyl-6-methoxybenzamideAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-6-methoxybenzoic acid (0.841 g, 5.0 mmol, 1.0 equiv), benzylamine (0.643 g, 6.0 mmol, 1.2 equiv), and diisopropylethylamine (1.935 g, 15.0 mmol, 3.0 equiv) in 50 mL of dichloromethane was added 2-chloro-1,3-dimethylimidazolinium chloride (1.099 g, 6.5 mmol, 1.3 equiv) at room temperature. The mixture was stirred at room temperature for 6 hours, poured into water, and extracted with dichloromethane. The organic solution was successively washed with aqueous saturated NaHCO3 and water. The organic layer was dried over MgSO4 and the solvent was removed by rotary evaporator. The residue was purified by column chromatography (silica gel, 2% 2.0 M ammonia MeOH solution in CH2Cl2) to give 2-Amino-N-benzyl-6-methoxybenzamide (0.593 g, 46%) as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.81 (s, 3H), 4.62 (s, 1H), 4.63 (s, 1H), 6.07 (vb.s., 2H), 6.19 (d, J=8.2 Hz, 1H), 6.32 (d, J=8.2 Hz, 1H), 7.07 (t, J=8.2 Hz, 1H), 7.14-7.54 (m, 5H), 8.05 (br. s., 1H); HPLC: tR=4.72 min, UV254=99%; HRMS (ESI): m/z calcd for C15H16N2O2 [M+1]+257.1296. Found 257.1294.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe organic solution was successively washed with aqueous saturated NaHCO3 and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed by rotary evaporator
  5. customThe residue was purified by column chromatography (silica gel, 2% 2.0 M ammonia MeOH solution in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-977e5d5d39b04d1dbbec049591e36c9f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741259B2

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