Triethylamine → HCID 66891597, compound

HRID 2369899Notes

Reaction equation

HRID 2369899 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[CH3:22][O:23][CH:24]([O:27][CH3:28])[CH2:25][NH2:26]>C1COCC1>[CH3:22][O:23][CH:24]([O:27][CH3:28])[CH2:25][NH:26][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Product 1

HCID 66891597HCID 66891597, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-chloro-3-nitrobenzoate (1.1 g, 4.9 mmol) from Step A above in THF (33 mL) was added triethylamine (0.8 mL, 6.0 mmol) followed by 2,2-dimethoxyethanamine (0.7 mL, 6.0 mmol) at room temperature. The reaction mixture was stirred overnight at reflux. The suspension was concentrated under reduced pressure and purified by column chromatography (silica gel, 0% to 10% ethyl acetate in hexanes) to afford methyl 2-(2,2-dimethoxyethylamino)-3-nitrobenzoate (1.4 g, 98%): 1H NMR (500 MHz, DMSO-d6) δ 8.39 (t, J=4.5 Hz, 8.08-8.05 (m, 2H), 6.83 (t, J=8.0 Hz, 1H), 4.54 (t, J=5.0 Hz, 1H), 3.87 (s, 3H), 3.31 (s, 6H), 2.93 (t, J=5.0 Hz, 1H).

Workup

  1. temperatureat reflux
  2. concentrationThe suspension was concentrated under reduced pressure
  3. custompurified by column chromatography (silica gel, 0% to 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-dd3a4ea4c5a54e7f9c092e4a32224293
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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