1-Naphthylamine → HCID 11694296, compound

HRID 2353575Notes

Reaction equation

HRID 2353575 reaction equation
[C:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH3:21][O:22][C:23](=[O:27])[C:24](Cl)=[O:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:21][O:22][C:23](=[O:27])[C:24]([NH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:25]

Participants

6

Reactant 4

HCID 86401-NaphthylamineHCID 79846Methyl chloroglyoxylateHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 11694296HCID 11694296, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask containing 1-naphthyl amine (0.1 g, 0.68 mmol) stirring in DCM (5 mL) was added DIEA (0.18 mL, 1.02 mmol) and chloro-oxo-acetic acid methyl ester (0.068 mL, 0.748 mmol). The mixture was allowed to stir at room temperature for 1 h. The reaction mixture was poured over saturated sodium bicarbonate and the layers separated. The aqueous layer was extracted twice more with 3×15 mL DCM. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo to afford a brown solid. The crude material was purified by flash chromatography (0-50% EtOAc:Hexanes on silica gel) to yield the desired product (0.14 g, 90%) as an off-white solid. Expected mass=229. Observed mass=230.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted twice more with 3×15 mL DCM
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto afford a brown solid
  7. customThe crude material was purified by flash chromatography (0-50% EtOAc:Hexanes on silica gel)

Sources & evidence

ORD record
ord-7857c98c1e894601b39872508b5d33ca
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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