1,2-Dichloroethane → HCID 18505298, compound

HRID 1925251Notes

Reaction equation

HRID 1925251 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Cl)CCl>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 18505298HCID 18505298, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-hydroxy-naphthalene-2-carboxylic acid (2.0 g, 10.6 mmol, Aldrich) and benzylamine (1.7 g, 15.9 mmol, Aldrich) in DMF (40 mL, Aldrich) at 0° C. was added EDC (3.05 g, 15.9 mmol, Aldrich). The reaction was warmed to RT and stirred for 16 h. The volatile portion was removed in vacuo. The residue was diluted with 100 mL of EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in EtOAc and passed through a short silica gel column and the filtrate was concentrated in vacuo. Recrystallization with 50% EtOAc/hexane provided the title compound as a white solid.

Workup

  1. customThe volatile portion was removed in vacuo
  2. additionThe residue was diluted with 100 mL of EtOAc
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc
  7. concentrationthe filtrate was concentrated in vacuo
  8. customRecrystallization with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-2815de76aec24c2499862e507c64385d
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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