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

HRID 714550Notes

Reaction equation

HRID 714550 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 583841432-amino-N-benzyl-6-methoxybenzamideYield 46.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8cae3cd804d141baa24329faf80cb8d0
Source dataset
uspto-grants-2015_11
Patent number
US09187457B2

Reaction notes

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