2-Methoxyethylamine → HCID 59353095, compound

HRID 1914704Notes

Reaction equation

HRID 1914704 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6]([OH:8])=O.Cl.CN(C)CCCN=C=NCC.[CH3:27][O:28][CH2:29][CH2:30][NH2:31]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6]([NH:31][CH2:30][CH2:29][O:28][CH3:27])=[O:8]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53002123-Methoxy-5-nitrobenzoic acid

Product 1

HCID 59353095HCID 59353095, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxy-5-nitrobenzoic acid (1 g; 5.1 mmol; 1 eq) DCM (40 mL) is added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (972 mg; 5.1 mmol; 1 eq). After 5 min, 2-methoxyethylamine (381 mg; 5.1 mmol; 1 eq) is added and the reaction mixture is stirred at room temperature for 2 h. The reaction mixture is then quenched with water and the expected product extracted with EtOAc. The organic phase is washed with an aqueous solution of Na2CO3 then dried over MgSO4. The solvent is evaporated to dryness to afford (1.3 g (100%) of the title compound as an orange oil. HPLC (max plot) 73.0%; Rt 2.98 min.

Workup

  1. customThe reaction mixture is then quenched with water
  2. extractionthe expected product extracted with EtOAc
  3. washThe organic phase is washed with an aqueous solution of Na2CO3
  4. dry with materialthen dried over MgSO4
  5. customThe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-c35e383d89f54b798ee602e7be7172ab
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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