Triethylamine → HCID 66891597, compound

HRID 2369919Notes

Reaction equation

HRID 2369919 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 and then the suspension was concentrated under reduced pressure. The crude material was 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, 1H), 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. customThe crude material was purified by column chromatography (silica gel, 0% to 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f60668f111ef41fbbdf2dc32d1652e1f
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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