O-Phenylenediamine → HCID 70114277, compound

HRID 868945Notes

Reaction equation

HRID 868945 reaction equation
[CH3:1][C:2]1[C:3]([CH2:12][CH2:13][C:14](O)=O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:17]1([NH2:24])[C:18]([NH2:23])=[CH:19][CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1>[NH:23]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:24]=[C:14]1[CH2:13][CH2:12][C:3]1[C:2]([CH3:1])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 3

HCID 7243O-PhenylenediamineHCID 10340Sodium CarbonateHCID 2581413-(3-methylquinoxalin-2-yl)propanoic acid

Product 1

HCID 70114277HCID 70114277, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

3-(3-Methylquinoxalin-2-yl)propanoic acid (98 mg, 0.45 mmol) and benzene-1,2-diamine (98 mg, 0.45 mmol) were suspended in 4 M HCl in 1,4-dioxane (6 mL) and heated in the microwave (150° C., 2.5 h). The crude reaction was poured into saturated aqueous Na2CO3 solution (30 mL) and extracted with EtOAc (3×50 mL). The organic layers were combined, washed with brine (1×50 mL), dried (Na2SO4), filtered and concentrated. The crude material was purified by RPLC (Gilson). Fractions containing the compound were combined, diluted with EtOAc and washed with saturated aqueous Na2CO3, dried (Na2SO4), filtered and concentrated to give 2-(2-(1H-benzo[d]imidazol-2-yl)ethyl)-3-methylquinoxaline (8 mg) as an orange oil. LC-MS m/z 289 (M+H+).

Workup

  1. customThe crude reaction
  2. extractionextracted with EtOAc (3×50 mL)
  3. washwashed with brine (1×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by RPLC (Gilson)
  8. additionFractions containing the compound
  9. additiondiluted with EtOAc
  10. washwashed with saturated aqueous Na2CO3
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-e1aad603e8d64a6d9d08400beb469181
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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