Phenethylamine → HCID 86698557, compound

HRID 1749010Notes

Reaction equation

HRID 1749010 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[C:12](OC(=O)C)(=O)[CH3:13].[CH2:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(=O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:8])[N:27]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]([CH3:13])=[N:11]2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 7918Acetic AnhydrideHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 86698557HCID 86698557, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

4-chloroanthranilic acid (6 g, 34.27 mmol) suspended in acetic anhydride (25 mL, 264.47 mmol) was refluxed for 3 h. The resulting solution was cooled to rt to give crystal formed. The solution was filtered and washed with excess of hexane to get light yellow needle crystal. The crystal was mixed with phenethylamine (4.6 mL, 36.15 mmol) in acetic acid (25 mL) and refluxed for 18.5 h. After 18.5 h, the reaction mixture was diluted with dichloromethane (50 mL) and washed with water (3×50 mL) and saturated aqueous NaHCO3 solution (7×40 mL). The organic layer dried over MgSO4 was concentrated to around 20 mL and added with excess of MeOH to get crystal formed. The solution was filtered to give title compound as white crystal (5.2 g, 50.8%). Rf=0.3 (ethyl acetate/hexane=1:2); mp 133-135° C. (recrystallized from methanol); 1H NMR (400 MHz, DMSO-d6) δ 2.46 (s, 3H, CH3), 2.96 (t, J=8 Hz, 2H, CH2), 4.20 (t, J=8 Hz, 2H, CH2), 7.23-7.25 (m, 3H, ArH), 7.28-7.32 (m, 2H, ArH), 7.49 (dd, 1H, J=8.4, 2 Hz, 7.60 (d, J=2 Hz, 1H, ArH), 8.09 (d, J=8.4 Hz, 1H, ArH); 13C NMR (50 MHz, DMSO-d6) δ 23.2, 33.9, 46.2, 119.2, 126.1, 127.0, 127.1, 128.7, 129.1, 129.3, 138.7, 139.4, 148.6, 157.1, 160.9; ESIMS(+) m/z 299.0 [M+1]+. Anal. (C17H15ClN2O) C, H, N. Calcd: 68.34, 5.06, 9.38. Found: 68.56, 5.07, 9.57.

Workup

  1. temperaturewas refluxed for 3 h
  2. customto give crystal
  3. customformed
  4. filtrationThe solution was filtered
  5. washwashed with excess of hexane
  6. customto get light yellow needle crystal
  7. temperaturerefluxed for 18.5 h
  8. washwashed with water (3×50 mL) and saturated aqueous NaHCO3 solution (7×40 mL)
  9. dry with materialThe organic layer dried over MgSO4
  10. concentrationwas concentrated to around 20 mL
  11. additionadded with excess of MeOH
  12. customto get crystal
  13. customformed
  14. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-4f59abaa222945c7988ac5587bca10a9
Source dataset
uspto-grants-2015_10
Patent number
US09155739B2

Reaction notes

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