3,4-Dichlorobenzoic acid → HCID 71541849, compound

HRID 1023163Notes

Reaction equation

HRID 1023163 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][C:14]([NH:16][NH2:17])=[O:15])[CH:8]=2)[NH:3]1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:22](O)=O.C(N(CC)CC)C.CCCP(=O)=O>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([C:22]2[O:15][C:14]([CH2:13][O:12][C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH:11]=[CH:10]4)=[N:16][N:17]=2)[CH:25]=[CH:26][C:27]=1[Cl:28]

Participants

6

Reactant 4

HCID 58173,4-Dichlorobenzoic acidHCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 86680404HCID 86680404, compound

Product 1

HCID 71541849HCID 71541849, compoundYield 4.81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2-((2-oxo-1,2-dihydroquinolin-6-yl)oxy)acetohydrazide (0.2 g, 0.858 mmol) and 3,4-dichlorobenzoic acid (0.163 g, 0.858 mmol)) in DMF (8 mL) was added triethylamine (0.598 mL, 4.29 mmol) and propylphosphonic anhydride (T3P) (0.819 g, 2.57 mmol). The reaction mixture was heated at 100° C. overnight under N2 atm. The reaction mixture was concentrated to remove solvent and ice-cold water was added. The precipitate was filtered and washed with water to afford a brown solid. The crude product was purified by preparative HPLC on a C18 reverse phase column (ACN-NH4OAc method) to give 6-((5-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl)methoxy)quinolin-2(1H)-one as a white solid (0.016 g, 4.81%). 1H NMR: 400 MHZ, DMSO-d6: δ 5.51 (s, 1H), 6.52 (d, J=9.60 Hz, 1H), 7.27-7.31 (m, 2H), 7.43 (d, J=2.40 Hz, 1H), 7.83-7.92 (m, 2H), 8.00 (dd, J=1.60, 8.40 Hz, 1H), 8.21 (d, J=1.60 Hz, 1H), 11.68 (s, 1H). LCMS: RT 1.92 min. LCMS (ES-API), m/z 390.0 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove solvent and ice-cold water
  3. additionwas added
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customto afford a brown solid
  7. customThe crude product was purified by preparative HPLC on a C18 reverse phase column (ACN-NH4OAc method)

Sources & evidence

ORD record
ord-20e63d7f0e754c8198839da486bc0165
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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