Triethylamine → HCID 70980720, compound

HRID 1749078Notes

Reaction equation

HRID 1749078 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9](Cl)[N:8]=1)[CH3:2].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>CC#N>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]([NH:30][CH2:29][C:28]2[CH:31]=[CH:32][C:33]([O:35][CH3:36])=[CH:34][C:27]=2[O:26][CH3:25])[N:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 13245756Ethyl 2-[(6-chloro-3-nitro-2-pyridinyl)oxy]acetate

Product 1

HCID 70980720HCID 70980720, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cooled (˜10° C.) solution of (6-chloro-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (8.0 g, 30.8 mmol) in MeCN (80 mL) was added a solution of triethylamine (6.4 mL, 46 mmol) and 2,4-dimethoxybenzylamine (5.5 mL, 37 mmol). The mixture was then stirred for 16 hours at ambient temperature and then concentrated in vacuo. The residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution. The EtOAc layer was then washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified using SiO2 chromatography (10-50% EtOAc/Petrol) to give [6-(2,4-dimethoxy-benzylamino)-3-nitro-pyridin-2-yloxy]acetic acid ethyl ester (9.53 g) as a yellow solid. MS: [M+H]+ 392

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution
  3. washThe EtOAc layer was then washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-e92a3be54b6d4d42b4c82659aa8857bc
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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